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Journal articles on the topic 'Acide isocyanique'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Reguera, Leslie, Cecilia I. Attorresi, Javier A. Ramírez, and Daniel G. Rivera. "Steroid diversification by multicomponent reactions." Beilstein Journal of Organic Chemistry 15 (June 6, 2019): 1236–56. http://dx.doi.org/10.3762/bjoc.15.121.

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Reports on structural diversification of steroids by means of multicomponent reactions (MCRs) have significantly increased over the last decade. This review covers the most relevant strategies dealing with the use of steroidal substrates in MCRs, including the synthesis of steroidal heterocycles and macrocycles as well as the conjugation of steroids to amino acids, peptides and carbohydrates. We demonstrate that steroids are available with almost all types of MCR reactive functionalities, e.g., carbonyl, carboxylic acid, alkyne, amine, isocyanide, boronic acid, etc., and that steroids are suitable starting materials for relevant MCRs such as those based on imine and isocyanide. The focus is mainly posed on proving the amenability of MCRs for the diversity-oriented derivatization of naturally occurring steroids and the construction of complex steroid-based platforms for drug discovery, chemical biology and supramolecular chemistry applications.

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2

Chen, Zhen-Bang, Kui Liu, Fang-Ling Zhang, Qing Yuan, and Yong-Ming Zhu. "Palladium-catalyzed oxidative coupling of arylboronic acid with isocyanide to form aromatic carboxylic acids." Organic & Biomolecular Chemistry 15, no. 38 (2017): 8078–83. http://dx.doi.org/10.1039/c7ob01428g.

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3

Rainoldi, Giulia, Giordano Lesma, Claudia Picozzi, Leonardo Lo Presti, and Alessandra Silvani. "One step access to oxindole-based β-lactams through Ugi four-center three-component reaction." RSC Advances 8, no. 61 (2018): 34903–10. http://dx.doi.org/10.1039/c8ra08165d.

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4

Ghashghaei, Ouldouz, Consiglia Annamaria Manna, Esther Vicente-García, Marc Revés, and Rodolfo Lavilla. "Studies on the interaction of isocyanides with imines: reaction scope and mechanistic variations." Beilstein Journal of Organic Chemistry 10 (January 6, 2014): 12–17. http://dx.doi.org/10.3762/bjoc.10.3.

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The interaction of imines with isocyanides has been studied. The main product results from a sequential process involving the attack of two units of isocyanide, under Lewis acid catalysis, upon the carbon–nitrogen double bond of the imine to form the 4-membered ring system. The scope of the reaction regarding the imine and isocyanide ranges has been determined, and also some mechanistic variations and structural features have been described.

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5

Hu, Langxi, Weijun Gui, Zichen Liu, and Baishan Jiang. "Synthesis of 3-aryl-2-aminoquinolines: palladium-catalyzed cascade reactions of gem-dibromovinylanilines with tert-butyl isocyanide and arylboronic acids." RSC Adv. 4, no. 72 (2014): 38258–62. http://dx.doi.org/10.1039/c4ra05670a.

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6

Paprocki, Daniel, Dominik Koszelewski, Anna Żądło, Peter Walde, and Ryszard Ostaszewski. "Environmentally friendly approach to α-acyloxy carboxamides via a chemoenzymatic cascade." RSC Advances 6, no. 72 (2016): 68231–37. http://dx.doi.org/10.1039/c6ra13078j.

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7

Anary-Abbasinejad, Mohammad, Maryam Rasekh, and Hossein Anaraki-Ardakani. "Four-Component Reaction of Isocyanides, Acetylenic Esters, and Carboxylic Acids for the Synthesis of Functionalised 2,5-diaminofurans." Journal of Chemical Research 2009, no. 5 (May 2009): 271–73. http://dx.doi.org/10.3184/030823409x439735.

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An improved four-component reaction of isocyanides is described. The reaction between two equivalents of an isocyanide, dialkyl acetylenedicarboxylates and aliphatic carboxylic acids at room temperature leads to 2,5-diaminofuran derivatives in good yields.

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8

Marandi, Ghasem. "Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde." Combinatorial Chemistry & High Throughput Screening 21, no. 4 (May 25, 2018): 298–301. http://dx.doi.org/10.2174/1386207321666180416153112.

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Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

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9

Cao, Ming, Qing-Hu Teng, Zhi-Wei Xi, Li-Qiu Liu, Ren-Yong Gu, and Ying-Chun Wang. "Facile synthesis of 2-alkynyl oxazoles via a Ce(OTf)3-catalyzed cascade reaction of alkynyl carboxylic acids with tert-butyl isocyanide." Organic & Biomolecular Chemistry 18, no. 4 (2020): 655–59. http://dx.doi.org/10.1039/c9ob02337b.

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We developed an efficient and novel protocol to synthesize 2-alkynyloxazoles from tert-butyl isocyanide and alkynyl carboxylic acids, and these diversely functionalized oxazoles showed a certain degree of biological activity.

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10

Wang, Zikun, Xihe Bi, Yongjiu Liang, Peiqiu Liao, and Dewen Dong. "A copper-catalyzed formal O–H insertion reaction of α-diazo-1,3-dicarbonyl compounds to carboxylic acids with the assistance of isocyanide." Chem. Commun. 50, no. 30 (2014): 3976–78. http://dx.doi.org/10.1039/c4cc00402g.

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Straightforward synthetic access to α-acyloxy-1,3-dicarbonyl compounds is described via a novel Cu(ii)-catalyzed and isocyanide-assisted formal O–H insertion reaction of α-diazocarbonyl compounds to carboxylic acids.

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11

Arnold, DP, RFC Brown, LJ Nitschinsk, P. Perlmutter, and HK Tope. "Derivatives of 4-(Aminomethyl)pyrrole-3-carboxylic Acid." Australian Journal of Chemistry 47, no. 5 (1994): 975. http://dx.doi.org/10.1071/ch9940975.

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12

Al Otaibi, Ahmed, Fiona M. Deane, Cecilia C. Russell, Lacey Hizartzidis, Siobhann N. McCluskey, Jennette A. Sakoff, and Adam McCluskey. "A methanol and protic ionic liquid Ugi multicomponent reaction path to cytotoxic α-phenylacetamido amides." RSC Advances 9, no. 14 (2019): 7652–63. http://dx.doi.org/10.1039/c9ra00118b.

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The Ugi reaction (aldehyde, amine, isocyanide and an ethanoic acid) in the protic ionic liquids ethylammonium nitrate (EAN) and propylammonium nitrate (PAN) gave excellent yields of α-phenylacetamido amides.

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13

Paprocki, Daniel, Dominik Koszelewski, Peter Walde, and Ryszard Ostaszewski. "Efficient Passerini reactions in an aqueous vesicle system." RSC Advances 5, no. 124 (2015): 102828–35. http://dx.doi.org/10.1039/c5ra22258c.

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The formation of α-acyloxy carboxamides from a carboxylic acid, an aldehyde and an isocyanide (Passerini reaction) was investigated in aqueous solution in the presence of different types of surfactants.

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14

Neochoritis, Constantinos G., Tryfon Zarganes-Tzitzikas, Michaela Novotná, Tatiana Mitríková, Zefeng Wang, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, and Alexander Dömling. "Isocyanide-Based Multicomponent Reactions of Free Phenylboronic Acids." European Journal of Organic Chemistry 2019, no. 35 (August 29, 2019): 6132–37. http://dx.doi.org/10.1002/ejoc.201901187.

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15

Zhang, Ling-Juan, Mei-Chen Xu, Jie Liu, and Xian-Ming Zhang. "Tandem cycloaddition–decarboxylation of α-keto acid and isocyanide under oxidant-free conditions towards monosubstituted oxazoles." RSC Advances 6, no. 77 (2016): 73450–53. http://dx.doi.org/10.1039/c6ra16031j.

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An efficient method, tandem [3 + 2] cycloaddition–decarboxylation of α-keto acid and isocyanide promoted by copper salt, has been developed for constructing monosubstituted oxazole. The elegant approach ingeniously avoids consuming excess oxidants.

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16

Anary-Abbasinejad, Mohammad, Maryam Kamali-Gharamaleki, and Alireza Hassanabadi. "Three-component reaction of Cyclohexyl Isocyanide, Barbituric Acid and Aryl Aldehydes; Synthesis of N-cyclohexyl-N-[aryl-(2,4,6-trioxohexahydropyrimidin-5-yl)methyl]formamides." Journal of Chemical Research 2007, no. 10 (October 2007): 594–97. http://dx.doi.org/10.3184/030823407x256136.

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Three-component reaction of cyclohexyl isocyanide, barbituric acid and different aldehydes, in a mixture of water: acetonitrile (1:1) as solvent, produces the corresponding N-cyclohexyl- N-[aryl-(2,4,6-trioxohexahydropyrimidin-5-yl)methyl]formamides in excellent yields.

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17

Onwukamike, Kelechukwu Nnabuike, Stéphane Grelier, Etienne Grau, Henri Cramail, and Michael A. R. Meier. "On the direct use of CO2in multicomponent reactions: introducing the Passerini four component reaction." RSC Advances 8, no. 55 (2018): 31490–95. http://dx.doi.org/10.1039/c8ra07150k.

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We introduce a novel isocyanide-based multicomponent reaction, the Passerini four component reaction (P-4CR), by replacing the carboxylic acid component of a conventional Passerini three component reaction (P-3CR) with an alcohol and CO₂.

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18

König, Stephan, and Ivar Ugi. "Vernetzung wäßriger Alginsäure mittels der Vierkomponenten-Kondensation unter Einschluß-Immobilisierung von Enzymen / Crosslinking of Aqueous Alginic Acid by Four Component Condensation with Inclusion Immobilization of Enzymes." Zeitschrift für Naturforschung B 46, no. 9 (September 1, 1991): 1261–66. http://dx.doi.org/10.1515/znb-1991-0921.

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The four component condensation (4 CC, Ugi reaction) of aqueous alginic acid with formaldehyde, difunctional amine and isocyanide components produces a gel. Enzymes, e.g. “acidic phosphatase” (AP) and L-(+)-lactate dehydrogenase (LDH), can be immobilized by inclusion in the above crosslinked alginic acid. The enzymes retain some of their activity (LDH: 8-10%; AP: 82-87%).

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19

Ding, Ming-Wu, Zhi-Lin Ren, Mei Sun, and Zhi-Rong Guan. "New Efficient Synthesis of 1,2,4-Trisubstituted Furans by a Sequential Passerini/Wittig/Isomerization Reaction Starting from Baylis–Hillman β-Bromo Aldehydes." Synlett 29, no. 01 (August 25, 2017): 106–10. http://dx.doi.org/10.1055/s-0036-1588564.

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A new and efficient synthesis of 1,2,4-trisubstituted furans from a Baylis–Hillman β-bromo aldehyde, an acid, an isocyanide, and methyl(diphenyl)phosphine, by a sequential Passerini condensation, Wittig reaction, and isomerization in the presence of triethylamine is reported.

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20

El Kaïm, Laurent, Laurence Grimaud, Maxime Vitale, Sudipta Ponra, Aude Nyadanu, and Sylvie Maurin. "TiCl4-Mediated Synthesis of 3,4-Hetero-Disubstituted Isocoumarins by Means of Isocyanide Insertion Reactions." Synthesis 50, no. 06 (December 13, 2017): 1331–42. http://dx.doi.org/10.1055/s-0036-1591733.

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The isocyanide insertion into sulfanyl-phthalides under Lewis acid conditions is reported with full details. This sequential three-component reaction affords a new straightforward and highly convenient method for the preparation of 3-amino-4-sulfanyl isocoumarins, the potential of which is still unexplored.

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21

Filippou, Alexander Constantin, and Walter Grünleitner. "Säure-induzierte CC-Kupplung von Isocyanid-Liganden in homoleptischen Alkylisocyanid-Komplexen von Mo(0) und W(0) / Acid-Induced CC-Coupling of Isocyanide Ligands in Homoleptic Alkylisocyanide Complexes of Mo(0) and W(0)." Zeitschrift für Naturforschung B 46, no. 2 (February 1, 1991): 216–30. http://dx.doi.org/10.1515/znb-1991-0216.

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Reactions of the electron-rich, homoleptic alkylisocyanide complexes M(R N C)6 (1a-2b) (1: M = Mo, 2: M = W; a: R = Et, b: R = tBu) with electrophiles have been studied. A coupling of two isocyanide ligands to a complexed alkyne ligand is observed, when M(R N C)6 is treated with two equivalents of HX(X = Br, I) and leads to the bis(alkylamino)acetylene complexes [X (R N C )4M[η2-R(H)NC ≡ CN(H)R]]X (3a′-4b″) (3: M = Mo, 4: M = W). Treatment of W (EtNC)6 (2a) and W (tBuNC)6 (2b) with one equivalent of Me3SiOTf results in the quantitative formation of the aminocarbyne complexes [(EtNC)5W ≡ CN (SiMe3)Et]OTf (6c) and [(tBuNC)5W ≡ C N (SiMe3)tBu]OTf (6d), respectively. In comparison, an equilibrium between W(tBuNC)6 (2b) and the aminocarbyne complex [(tBuNC)5W ≡ C N (SiMe3)tBu]Cl (6e) is found, when 2b is treated with Me3SiCl. The compounds 6c and 6d are structurally related to the aminocarbyne complexes [(EtNC)5M ≡ C N E t2]BF4 (5a: M = Mo, 6a: M = W) and [(tBuNC)5W ≡ C N (Et)Bu]BF4 (6b), which are obtained from ethylation of M (EtNC)6 (1a, 2a) and W (tBuNC)6 (2b) with Et3OBF4. 5a and 6a undergo with HI a carbyne-isocyanide coupling reaction to give the alkyne complexes [I(EtNC)4Mo[η2-Et2NC≡CN(H)Et]]BF4 (7a) and [I(EtNC)4W[η2-Et2NC≡CN(H)Et]]BF4 (8a), respectively. Similar reactivity is exhibited by 6b, which yields with HI the alkyne complex [I(tBuNC)4W[η2-tBu(Et)N C ≡ C N (H)tBu]]BF4 (8b). The reported transformation of a complexed isocyanide to an aminocarbyne and the acid-induced aminocarbyne-isocyanide coupling reaction are experimentally verified to be important steps in the reductive coupling of isocyanide ligands in [M(RNC)6X]+-complexes yielding the bis(alkylamino)acetylene compounds [X(R N C)4M[η2-R (H )N C ≡ C N (H )R ]]+.

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22

McAlees, A. J., K. Schwartzentruber, and A. Taylor. "Esterification of isocyanide carboxylic acids and hydrolysis of their esters." Journal of the Chemical Society, Perkin Transactions 1, no. 7 (1990): 2115. http://dx.doi.org/10.1039/p19900002115.

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23

Moni, Lisa, Luca Banfi, Andrea Basso, Alice Brambilla, and Renata Riva. "Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization." Beilstein Journal of Organic Chemistry 10 (January 17, 2014): 209–12. http://dx.doi.org/10.3762/bjoc.10.16.

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An operationally simple protocol for the synthesis of 2,3-dihydrobenzo[f][1,4]oxazepin-3-ones, based on an Ugi reaction of an ortho-(benzyloxy)benzylamine, glycolic acid, an isocyanide and an aldehyde, followed by an intramolecular Mitsunobu substitution was developed. The required ortho-(benzyloxy)benzylamines have been in situ generated from the corresponding azides, in turn prepared in high yields from salicylic derivatives.

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24

Lang, Markus A., Peter Mayer, and Wolfgang Beck. "Tris(2-isocyanocarbonsäureester)-Halbsandwich-Komplexe [(Aren)M(CNCHR1CO2R2)3]2+ (M = Ru, Rh, Ir) / Tris(2-isocyanocarboxylic Acid Ester) – Halfsandwich Complexes [(arene)M(CNCHR1CO2R2)3]2+ (M = Ru, Rh, Ir)." Zeitschrift für Naturforschung B 59, no. 2 (February 1, 2004): 190–95. http://dx.doi.org/10.1515/znb-2004-0211.

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By reaction of chloro bridged halfsandwich complexes with silver salts and subsequent addition of isocyanocarboxylic acid esters the isocyanide complexes [(arene)M(CNCHR1CO2R2)3]2+(X−)2 (arene = C6Me6, p-cymene, M = Ru; arene = C5Me5, M = Rh, Ir), (R1 = H, Me, CHMe2, CH2Ph, X = BF4, CF3 SO3) were prepared and characterized. The structure of [(C5Me5) Ir(CNCH2CO2Et)3]2+(CF3SO3−)2 was determined by X-ray structure analysis.

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25

Keykha, Ghodsyeh, Mohammad R. Hosseini-Tabatabaei, and Alireza Hassanabadi. "Synthesis of 1H-Chromeno[2,3-d]Pyrimidine-5-Carboxamides under Solvent-Free Conditions at Ambient Temperature." Journal of Chemical Research 41, no. 2 (February 2017): 85–87. http://dx.doi.org/10.3184/174751917x14849228329079.

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Good yields of six 1H-chromeno[2,3-d]pyrimidine-5-carboxamides were obtained via the two-stage, one-pot reaction of an alkyl isocyanide with the initially formed condensation product of 1,3-dimethyl barbituric acid and a salicylaldehyde under solvent-free conditions at ambient temperature. This procedure has a number of advantages, such as short reaction time and easy work-up. Also, the present method does not involve any hazardous organic solvent.

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26

Alizadeh, Abdolali, Kaveh Amir Ashjaee Asalemi, and Mohammadreza Halvagar. "Intramolecular Diels–Alder and [3+2] Cycloaddition Reactions in the One-Pot Synthesis of Epoxypyrrolo[3,4-g]indazoles." Synthesis 51, no. 15 (April 10, 2019): 2936–44. http://dx.doi.org/10.1055/s-0037-1612426.

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A one-pot approach for the synthesis of epoxypyrrolo[3,4-g]indazoles is presented. The first step was initiated by a three-component reaction of an isocyanide, a dialkyl acetylenedicarboxylate, and 2-furancarboxylic acid, and led to 1,3-dioxoepoxyisoindole, followed by the addition of hydrazonoyl chloride through a [3+2]-cycloaddition reaction in the second step. The key step in the formation of final compound involves a bicyclization strategy through intramolecular Diels–Alder (IMDA) reaction.

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27

Zhang, Jian, Peiyuan Yu, Shao-Yu Li, He Sun, Shao-Hua Xiang, Jun (Joelle) Wang, Kendall N. Houk, and Bin Tan. "Asymmetric phosphoric acid–catalyzed four-component Ugi reaction." Science 361, no. 6407 (September 13, 2018): eaas8707. http://dx.doi.org/10.1126/science.aas8707.

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The Ugi reaction constructs α-acylaminoamide compounds by combining an aldehyde or ketone, an amine, a carboxylic acid, and an isocyanide in a single flask. Its appealing features include inherent atom and step economy together with the potential to generate products of broad structural diversity. However, control of the stereochemistry in this reaction has proven to be a formidable challenge. We describe an efficient enantioselective four-component Ugi reaction catalyzed by a chiral phosphoric acid derivative that delivers more than 80 α-acylaminoamides in good to excellent enantiomeric excess. Experimental and computational studies establish the reaction mechanism and origins of stereoselectivity.

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28

Ramírez-López, Sandra C., and Rocío Gámez-Montaño. "Synthesis One Pot of Alkyne-2-Chloroquinoline via a Passerini Reaction." Proceedings 41, no. 1 (November 18, 2019): 76. http://dx.doi.org/10.3390/ecsoc-23-06700.

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A series of six new alkyne-2-chloroquinolines were synthesized in moderate yields (40%–65%) via the Passerini three-component reaction (P-3CR) under mild green conditions. The P-3CR takes place when a carboxylic acid, an oxo compound (aldehyde or ketone), and an isocyanide react to give α-acyloxy carboxamides. Recently it has been reported that small molecules containing alkynes promote interactions with different proteins in cells facilitating the detection or identification of protein targets.

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29

Shaabani, Ahmad, Hassan Farhid, Mohammad Mahdi Rostami, and Behrouz Notash. "Synthesis of Depsipeptides via Isocyanide-Based Consecutive Bargellini–Passerini Multicomponent Reactions." SynOpen 05, no. 03 (June 22, 2021): 167–72. http://dx.doi.org/10.1055/a-1533-3823.

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AbstractAn efficient and straightforward approach has been established for the preparation of a new class of depsipeptide structures via isocyanide-based consecutive Bargellini–Passerini multicomponent reactions. 3-Carboxamido-isobutyric acids bearing an amide bond were obtained via Bargellini multicomponent reaction from isocyanides, acetone, and chloroform in the presence of sodium hydroxide. Next, via a Passerini multicomponent-reaction strategy, a new class of depsipeptides was synthesized using the Bargellini reaction products, isocyanides, and aldehydes. The depsipeptides thus prepared have more flexible structures than their pseudopeptidic analogues.

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30

Fan, Xuesen, Yanzhen Li, Xinying Zhang, Guirong Qu, and Jianji Wang. "A novel and green version of the Passerini reaction in an ionic liquid ([bmim][BF4])." Canadian Journal of Chemistry 84, no. 5 (May 1, 2006): 794–99. http://dx.doi.org/10.1139/v06-070.

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The Passerini three-component condensation among a carboxylic acid (1), an aldehyde or ketone (2), and an isocyanide (3) was carried out for the first time in an ionic liquid, [bmim][BF4], and a series of acyloxycarboxamides were obtained through this reaction. The method presented herein has the advantages of high efficiency, a greener nature, and a simple operational procedure. Moreover, the ionic liquid can be easily recovered and reused for several runs without obvious loss of efficiency.Key words: Passerini reaction, acyloxycarboxamides, ionic liquid, green synthesis.

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31

Mueller, Louis G., Allen Chao, Embarek AlWedi, and Fraser F. Fleming. "One-step synthesis of imidazoles from Asmic (anisylsulfanylmethyl isocyanide)." Beilstein Journal of Organic Chemistry 17 (June 24, 2021): 1499–502. http://dx.doi.org/10.3762/bjoc.17.106.

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Substituted imidazoles are readily prepared by condensing the versatile isocyanide Asmic, anisylsulfanylmethylisocyanide, with nitrogenous π-electrophiles. Deprotonating Asmic with lithium hexamethyldisilazide effectively generates a potent nucleophile that efficiently intercepts nitrile and imine electrophiles to afford imidazoles. In situ cyclization to the imidazole is promoted by the conjugate acid, hexamethyldisilazane, which facilitates the requisite series of proton transfers. The rapid formation of imidazoles and the interchange of the anisylsulfanyl for hydrogen with Raney nickel make the method a valuable route to mono- and disubstituted imidazoles.

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32

Basiony, Mostafa, Yan Yang, Guoyu Liu, Xiao-Dong Gao, and Hideki Nakanishi. "Studies on the Properties of the Sporulation Specific Protein Dit1 and Its Product Formyl Tyrosine." Journal of Fungi 6, no. 2 (June 3, 2020): 77. http://dx.doi.org/10.3390/jof6020077.

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The dityrosine layer is a unique structure present in the spore wall of the budding yeast Saccharomyces cerevisiae. The primary constituent of this layer is bisformyl dityrosine. A sporulation-specific protein, Dit1 is localized in the spore cytosol and produces a precursor of bisformyl dityrosine. Although Dit1 is similar to isocyanide synthases, the loss of Dit1 is not rescued by heterologous expression of the Pseudomonas aeruginosa isocyanide synthase, PvcA, indicating that Dit1 does not mediate isocyanidation. The product of Dit1 is most likely formyl tyrosine. Dit1 can produce its product when it is expressed in vegetative cells; however, formyl tyrosine was not detected in the crude cell lysate. We reasoned that formyl tyrosine is unstable and reacts with some molecule to form formyl tyrosine-containing molecules in the cell lysate. In support of this hypothesis, formyl tyrosine was detected when the lysate was hydrolyzed with a mild acid. The same property was also found for bisformyl dityrosine. Bisformyl dityrosine molecules assemble to form the dityrosine layer by an unknown mechanism. Given that bisformyl dityrosine can be released from the spore wall by mild hydrolysis, the process of formyl tyrosine-containing molecule formation may resemble the assembly of the dityrosine layer.

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33

Moriguchi, Tetsuji, Venkataprasad Jalli, Suvratha Krishnamurthy, Akihiko Tsuge, and Kenji Yoja. "Crystal structure of (tert-butylcarbamoyl)(4-chloro-2-oxo-2H-chromen-3-yl)methyl acetate." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (November 28, 2015): o1002. http://dx.doi.org/10.1107/s2056989015021982.

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In the title compound, C17H18ClNO5, which was synthesized by reacting 4-chloro-3-formylcoumarin, acetic acid andtert-butyl isocyanide, the acetamido side chain is convoluted with ring-to-side chain C—C—C—C, C—C—C—N and C—C—N—C torsion angles of −123.30 (14), −135.73 (12) and 176.10 (12)°, respectively. In the crystal, N—H...O and weak C—H...O hydrogen bonds are present, which together with π–π coumarin-ring interactions [ring centroid separations = 3.4582 (8) and 3.6421 (9) Å], give rise to a layered structure lying parallel to (001).

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34

Mamaghani, Manouchehr, Nosrat O. Mahmoodi, Farhad Shirini, Abbas Azimi-Roshan, and Azam Monfared. "“On Water” Sonochemical Multicomponent Synthesis of Novel Bioactive 1,1′-(Aryl)bis(2-(cyclohexylamino)-2-oxoethane-1,1-diyl) Di(alkanoates and benzoates)." Journal of Chemistry 2013 (2013): 1–8. http://dx.doi.org/10.1155/2013/125959.

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An expeditious, efficient, and ecofriendly ultrasound-promoted synthesis of a series of novel 1,1′-(aryl)bis(2-(cyclohexylamino)-2-oxoethane-1,1-diyl) di(alkanoate and benzoate) derivatives (6a–k), as useful building block candidates for natural products and drugs, is reported. The target compounds were prepared by the reaction of alkyl or aryl carboxylic acid, various bisaldehydes and isocyanocyclohexane in water using one-pot isocyanide-based multicomponent approach. This efficient protocol without using any catalyst furnished the products in short reaction times (4-5 min) and excellent yields (87–96%). The antibacterial activity of the selected products was also examined. Some products showed promising activities.

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Dömling, Alexander, Eman Abdelraheem, and Samad Khaksar. "Concise Synthesis of Macrocycles by Multicomponent Reactions." Synthesis 50, no. 05 (January 10, 2018): 1027–38. http://dx.doi.org/10.1055/s-0036-1590946.

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A short reaction pathway was devised to synthesize a library of artificial 18–27-membered macrocycles. The five-step reaction sequence involves ring opening of a cyclic anhydride with a diamine, esterification, coupling with an amino acid isocyanide, saponification, and, finally, macro-ring closure using an Ugi or, alternatively, a Passerini multicomponent reaction. Three out of the five steps allow for the versatile introduction of linker elements, side chains, and substituents with aromatic, heteroaromatic, and aliphatic character. The versatile pathway is described for 15 different target macrocycles on a mmol scale. Artificial macrocycles have recently become of great interest due to their potential to bind to difficult post-genomic targets.

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36

Villanueva-Kasis, Oscar, Denisse A. de Loera, Sandra L. Castañón-Alonso, Armando Domínguez-Ortiz, Leticia Lomas-Romero, Ilich A. Ibarra, Eduardo González-Zamora, and Alejandro Islas-Jácome. "Efficient Synthesis of New α-β-Unsaturated Alkyl-Ester Peptide-Linked Chiral Amines." Proceedings 9, no. 1 (November 14, 2018): 34. http://dx.doi.org/10.3390/ecsoc-22-05769.

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Four new α-β-unsaturated alkyl-ester chiral amines were synthesized in excellent yields (77–95%) via peptide couplings from their corresponding α-β-unsaturated alkyl-ester anilines and N-Boc protected chiral aminoacids. To our delight, these polyfunctionalized compounds are being used as starting reagents in Ugi-type three-component reactions (Ugi-3CR) together with alkyl- and aryl-aldehydes and a chain-ring tautomerizable amino acid-containing isocyanide to synthesize novel oxazole-based macrocycle precursors. Thus, the aim of this communication is to show our most recent results of the synthesis and use of new and complex chiral amines to assemble macrocyclic polypeptides with potential application in medicinal chemistry, such as the post-surgical antibiotic Vancomycin.

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37

Hassanabadi, Alireza, Mohammad Anary-Abbasinejad, Atefeh Ahmadi Niri, and Rozita Feizpoor. "The Use of Cyclohexyl Isocyanide in the Esterification of N-Benzoyl α-Amino Acids Derivatives." Journal of Chemical Research 35, no. 8 (August 2011): 468–70. http://dx.doi.org/10.3184/174751911x13129847175330.

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38

Chen, Yuda, Kuan-Lin Wu, Juan Tang, Axel Loredo, Jordan Clements, Jingqi Pei, Zane Peng, Ruchi Gupta, Xinlei Fang, and Han Xiao. "Addition of Isocyanide-Containing Amino Acids to the Genetic Code for Protein Labeling and Activation." ACS Chemical Biology 14, no. 12 (November 4, 2019): 2793–99. http://dx.doi.org/10.1021/acschembio.9b00678.

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39

Neo, Ana G., and Carlos F. Marcos. "Pyrrolidinodiones in Enol-Ugi, Enol-Passerini, and Anomalous Enol-Passerini Condensations." Proceedings 9, no. 1 (November 19, 2018): 6. http://dx.doi.org/10.3390/ecsoc-22-05864.

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In continuation of our recent research on the development of novel multicomponent reactions with isocyanides, we have used, for the first time, enols as the acid components in Ugi- and Passerini-type reactions. Thus, electron-poor pyrrolidinodiones react with aldehydes, amines, and isocyanides to give the enaminic four-component adducts. Conversely, in the absence of the amine component, careful control of the reaction conditions allows the involvement of one or two molecules of isocyanide to afford, selectively, either Passerini-type or pseudo-enol-Ugi-type products. These unprecedented condensations of isocyanides, aldehydes, amines, and 4-substituted pyrrolidine-2,3-diones constitute an excellent strategy for the preparation of new biologically relevant pyrrolidinones having peptidic or pseudo-peptidic groups on carbon 3.

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40

Koopmanschap, Gijs, Eelco Ruijter, and Romano VA Orru. "Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics." Beilstein Journal of Organic Chemistry 10 (March 4, 2014): 544–98. http://dx.doi.org/10.3762/bjoc.10.50.

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In the recent past, the design and synthesis of peptide mimics (peptidomimetics) has received much attention. This because they have shown in many cases enhanced pharmacological properties over their natural peptide analogues. In particular, the incorporation of cyclic constructs into peptides is of high interest as they reduce the flexibility of the peptide enhancing often affinity for a certain receptor. Moreover, these cyclic mimics force the molecule into a well-defined secondary structure. Constraint structural and conformational features are often found in biological active peptides. For the synthesis of cyclic constrained peptidomimetics usually a sequence of multiple reactions has been applied, which makes it difficult to easily introduce structural diversity necessary for fine tuning the biological activity. A promising approach to tackle this problem is the use of multicomponent reactions (MCRs), because they can introduce both structural diversity and molecular complexity in only one step. Among the MCRs, the isocyanide-based multicomponent reactions (IMCRs) are most relevant for the synthesis of peptidomimetics because they provide peptide-like products. However, these IMCRs usually give linear products and in order to obtain cyclic constrained peptidomimetics, the acyclic products have to be cyclized via additional cyclization strategies. This is possible via incorporation of bifunctional substrates into the initial IMCR. Examples of such bifunctional groups are N-protected amino acids, convertible isocyanides or MCR-components that bear an additional alkene, alkyne or azide moiety and can be cyclized via either a deprotection–cyclization strategy, a ring-closing metathesis, a 1,3-dipolar cycloaddition or even via a sequence of multiple multicomponent reactions. The sequential IMCR-cyclization reactions can afford small cyclic peptide mimics (ranging from four- to seven-membered rings), medium-sized cyclic constructs or peptidic macrocycles (>12 membered rings). This review describes the developments since 2002 of IMCRs-cyclization strategies towards a wide variety of small cyclic mimics, medium sized cyclic constructs and macrocyclic peptidomimetics.

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41

Shaabani, Ahmad, Ebrahim Soleimani, and Hamid Reza Khavasi. "An unexpected, novel, three-component reaction between isoquinoline, an isocyanide and strong CH-acids in water." Tetrahedron Letters 48, no. 27 (July 2007): 4743–47. http://dx.doi.org/10.1016/j.tetlet.2007.05.019.

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42

Hassanabadi, Alireza, Mohammad Anary-Abbasinejad, Atefeh Ahmadi Niri, and Rozita Feizpoor. "The use of cyclohexyl isocyanide in the esterification of N-benzoyl α-amino acids derivatives." Journal of Chemical Research 35, no. 8 (August 1, 2011): 468–70. http://dx.doi.org/10.3184/174751911x13103888466593.

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43

Ramos-Tomillero, Iván, Marisa K. Sánchez, Hortensia Rodríguez, and Fernando Albericio. "Structure-Acid Lability Relationship of N-alkylated α,α-dialkylglycine Obtained via a Ugi Multicomponent Reaction." Molecules 26, no. 1 (January 2, 2021): 197. http://dx.doi.org/10.3390/molecules26010197.

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Using the classical Ugi four-component reaction to fuse an amine, ketone, carboxylic acid, and isocyanide, here we prepared a short library of N-alkylated α,α-dialkylglycine derivatives. Due to the polyfunctionality of the dipeptidic scaffold, this highly steric hindered system shows an interesting acidolytic cleavage of the C-terminal amide. In this regard, we studied the structure-acid lability relationship of the C-terminal amide bond (cyclohexylamide) of N-alkylated α,α-dialkylglycine amides 1a–n in acidic media and, afterward, it was established that the most important structural features related to its cleavage. Then, it was demonstrated that electron-donating effects in the aromatic amines, flexible acyl chains (Gly) at the N-terminal and the introduction of cyclic compounds into dipeptide scaffolds, increased the rate of acidolysis. All these effects are related to the ease with which the oxazolonium ion intermediate forms and they promote the proximity of the central carbonyl group to the C-terminal amide, resulting in C-terminal amide cleavage. Consequently, these findings could be applied for the design of new protecting groups, handles for solid-phase synthesis, and linkers for conjugation, due to its easily modulable and the fact that it allows to fine tune its acid-lability.

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44

Hanušová, Kristýna, Lukáš Vápenka, Jaroslav Dobiáš, and Linda Mišková. "Development of antimicrobial packaging materials with immobilized glucose oxidase and lysozyme." Open Chemistry 11, no. 7 (July 1, 2013): 1066–78. http://dx.doi.org/10.2478/s11532-013-0241-4.

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AbstractPackaging based on immobilization of antimicrobial enzymes provides a promising form of active packaging systems applicable in food processing. Glucose oxidase and lysozyme were immobilized by the Ugi reaction with cyclohexyl isocyanide and glutaraldehyde on polyamide and ionomer films partially hydrolysed by hydrochloric acid. The immobilization of the enzymes on the surface of films was confirmed by FT-IR spectroscopy and the films were characterized by the specific activity of the immobilized enzymes. The enzyme migration into model solutions and the effect of pH, temperature and storage time on the activity of immobilized enzyme were also evaluated. Immobilization of lysozyme onto polyamide and ionomer films resulted in the loss of enzyme activity. The polyamide and ionomer films with immobilized glucose oxidase inhibited the growth of bacteria Escherichia coli CNCTC 6859, Pseudomonas fluorescens CNCTC 5793, Lactobacillus helveticus CH-1, Listeria ivanovii CCM 5884 and Listeria innocua CCM 4030 on agar media.

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45

Sharifzadeh, Elaheh Sadat, and Nader Zabarjad Shiraz. "DFT studies on the diastereoselectivity of four-component Ugi reaction." Journal of Theoretical and Computational Chemistry 17, no. 06 (September 2018): 1850039. http://dx.doi.org/10.1142/s0219633618500396.

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In this study, mechanism and stereochemistry of four-component Ugi reaction was investigated theoretically. Structures of reagents, products, intermediates, and transition states were optimized at B3LYP/6-31[Formula: see text]G(d,p) level of theory. Mechanism and stereoselectivity of the reaction depended on several processes, including bond rotation, ring closure ring opening, acid-base, nucleophile-electrophile competitions, and rearrangements. These diverse phenomena were studied to provide a clearer picture of the mechanism of this valuable reaction, especially in terms of stereochemistry considerations. According to the results, (E)-oxazolidinols were considered as proper intermediates in Ugi reaction mechanism. In addition, the key point of diastereoselectivity of the reaction was under kinetic and thermodynamic controls of nucleophilic attack of isocyanide to less hindered re-face (E[Formula: see text] compared to 10.19[Formula: see text]kcal/mol for si-face) of chiral (E)-iminium ion.

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46

Gao, Qian, Wen-Juan Hao, Feng Liu, Shu-Jiang Tu, Shu-Liang Wang, Guigen Li, and Bo Jiang. "Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles." Chemical Communications 52, no. 5 (2016): 900–903. http://dx.doi.org/10.1039/c5cc08071a.

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A novel three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrano[3,4-c]pyrroles has been established from readily accessible 3-aroylacrylic acids, dialkyl acetylenedicarboxylates and isocyanides.

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47

Yavari, Issa, and Elham Karimi. "Synthesis of Functionalized 1‐Azadienes by Reaction of 2,6‐Dimethylphenyl Isocyanide and Acetylenic Esters in the Presence of CH Acids." Synthetic Communications 37, no. 7 (April 1, 2007): 1189–94. http://dx.doi.org/10.1080/00397910701199086.

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48

Liss, S. N., D. Brewer, A. Taylor, and G. A. Jones. "Antibiotic activity of an isocyanide metabolite of Trichoderma hamatum against rumen bacteria." Canadian Journal of Microbiology 31, no. 9 (September 1, 1985): 767–72. http://dx.doi.org/10.1139/m85-144.

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A metabolite of Trichoderma hamatum, 3-(3-isocyanocyclopent-2-enylidene)propionic acid, was tested for its effects on growth of and carbohydrate metabolism in 11 strains of functionally important rumen bacteria. To standardize the biological activity of this unstable metabolite, a rapid, aerobic disc diffusion assay was developed using Escherichia coli ATCC 11775. In an anaerobic broth dilution assay using a medium lacking rumen fluid and containing a soluble carbohydrate, the minimum inhibitory concentration of the metabolite which completely inhibited growth of the rumen bacteria for 18 h at 39 °C was generally < 10 μg∙mL−1; however, the minimum inhibitory concentrations for Megasphaera elsdenii B159 and Streptococcus bovis Pe18 were 10–25 and 25–64 μg∙mL−1, respectively. In general, the Gram-negative strains were more sensitive than the Gram positive. The minimum inhibitory concentration for Bacteroides ruminicola 23 grown with glucose was 1 μg∙mL−1; for B. ruminicola GA33 (glucose), B. succinogenes S85 (cellobiose), and Succinivibrio dextrinosolvens 24 (maltose), it was 2 μg∙mL−1. When added to a cellulose-containing rumen fluid medium, 1–4 μg∙mL−1 of the metabolite delayed cellulose hydrolysis by B. succinogenes S85, Ruminococcus albus 7, and R. flavefaciens FD1 for up to 4 days, and 6–7 μg∙mL−1 prevented hydrolysis for at least 1 month. In the presence of the metabolite, the proportion of acetate produced from soluble carbohydrate by the majority of strains increased, but with some strains net production of acetate decreased relative to production of other acidic fermentation products. If the metabolite gained entrance to the rumen, a concentration of as little as 1 μg∙mL−1 would probably cause a significant depression of the fermentation and result in nutritional deprivation of the animal.

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Agnew, Douglas W., Curtis E. Moore, Arnold L. Rheingold, and Joshua S. Figueroa. "Controlled cis Labilization of CO from Manganese(I) Mixed Carbonyl/Isocyanide Complexes: An Entry Point to Coordinatively Unsaturated Metallo-Lewis Acids." Organometallics 36, no. 2 (December 30, 2016): 363–71. http://dx.doi.org/10.1021/acs.organomet.6b00792.

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50

Nasiri, Farough, and Samiyeh Yosefdad. "Regioselective hydrolysis of ketenimines derived from NH-acids and acetylenic esters in the presence of tert-butyl isocyanide under neutral conditions." Monatshefte für Chemie - Chemical Monthly 139, no. 12 (June 26, 2008): 1457–61. http://dx.doi.org/10.1007/s00706-008-0954-9.

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