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Journal articles on the topic 'Isocyanides - Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Ahmadi, Fereshteh, and Ayoob Bazgir. "Synthesis of benzoimidazoquinazolines by cobalt-catalyzed isocyanide insertion–cyclization." RSC Advances 6, no. 66 (2016): 61955–58. http://dx.doi.org/10.1039/c6ra06828f.

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The synthesis of benzoimidazoquinazoline amines by the reaction of isocyanides and benzo[d]imidazol-anilines via a cobalt-catalyzed isocyanide insertion reaction into the two N–H active bonds is reported.

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2

Xiong, Jun, Qi-Xun Feng, Zhi-Ying Mu, et al. "Efficient Synthesis of 4H-3,1-Benzoxazine Derivatives via One-Pot Sequential Passerini-Azide/Palladium-Catalyzed Azide–Isocyanide Coupling/Cyclization Reaction." Synlett 31, no. 10 (2020): 1003–6. http://dx.doi.org/10.1055/s-0039-1690831.

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A new, one-pot method for the synthesis of 4H-3,1-benzoxazine derivatives has been developed. The Passerini-azide reactions of 2-azidobenzaldehydes, trimethylsilyl azide, and isocyanides produced azide intermediate without separation, which then reacted with isocyanides to give 4H-3,1-benzoxazine derivatives via a tandem one-pot palladium-catalyzed azide–isocyanide coupling/cyclization reaction in moderate to good yields.

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3

Vavsari, Vaezeh Fathi, Pegah Shakeri, and Saeed Balalaie. "Application of Chiral Isocyanides in Multicomponent Reactions." Current Organic Chemistry 24, no. 2 (2020): 162–83. http://dx.doi.org/10.2174/1385272824666200110095120.

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As one of the most important building blocks in organic synthesis, isocyanides come in for a wide range of transformations owing mostly to their unusual terminal carbon center adsorbed electrophiles, reacted with nucleophiles, get involved in radical reactions and coordinated with metal centers. The distinctive feature of isocyanide is its ready willingness to participate in multicomponent reactions (MCRs). MCRs represent a great tool in organic synthesis for the construction of new lead structures in a single procedure introducing both structural diversity and molecular complexity in only one

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4

Kim, Jungwon, and Soon Hyeok Hong. "Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis from ketones." Chemical Science 8, no. 3 (2017): 2401–6. http://dx.doi.org/10.1039/c6sc05266e.

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5

Kodama, Shintaro, Yuki Yamamoto, Yohsuke Kobiki, et al. "Transition-Metal-Catalyzed Diarylation of Isocyanides with Triarylbismuthines for the Selective Synthesis of Imine Derivatives." Materials 14, no. 15 (2021): 4271. http://dx.doi.org/10.3390/ma14154271.

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The transition-metal-catalyzed diarylation of isocyanides with triarylbismuthines was investigated in detail, and rhodium catalysts such as [RhCl(nbd)]2 were found to selectively afford N-alkyl diaryl ketimines. On the other hand, palladium-catalyzed diarylation proceeded with the incorporation of two molecules of isocyanide, preferentially yielding N,N’-dialkyl or N,N’-diaryl α-diimines. In addition, a cascade synthesis of 2,3-diarylquinoxalines starting from the palladium-catalyzed diarylation of isocyanides with triarylbismuthines was successfully achieved.

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6

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 (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 h

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7

Liu, Jian-Quan, Xuanyu Shen, Zhenhua Liu, and Xiang-Shan Wang. "Copper-catalyzed synthesis of arylcarboxamides from aldehydes and isocyanides: the isocyano group as an N1 synthon." Organic & Biomolecular Chemistry 15, no. 30 (2017): 6314–17. http://dx.doi.org/10.1039/c7ob01449j.

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For the first time, transition-metal-catalyzed isocyanide group acting as an N1 synthon rather than exhibiting the carbene-like reactivity was discovered, exploiting a new reactivity profile of isocyanides.

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8

Patil, Pravin, Maryam Ahmadian-Moghaddam, and Alexander Dömling. "Isocyanide 2.0." Green Chemistry 22, no. 20 (2020): 6902–11. http://dx.doi.org/10.1039/d0gc02722g.

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Isocyanides are important chemicals, with limited availability, thus reducing their general use. Our highly improved isocyanide synthesis performed on mole to μ-mole scale, individually or in a 96-well parallel fashion enables unprecedented exploration of novel chemistries.

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9

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 (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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10

Tailor, Yogesh Kumar, Sarita Khandelwal, Yogita Kumari, Kamlendra Awasthi, and Mahendra Kumar. "An efficient one pot three-component nanocatalyzed synthesis of spiroheterocycles using TiO2 nanoparticles as a heterogeneous catalyst." RSC Advances 5, no. 57 (2015): 46415–22. http://dx.doi.org/10.1039/c5ra04863j.

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An efficient, environmentally benign isocyanide-based domino protocol is presented for synthesizing spiroheterocycles with 2-amino benzothiazole/1,3,4-thiadiazole, cyclohexyl/tert-butyl isocyanides and isatines/cyclic carbonyls, catalyzed by recyclable nanocrystalline TiO<sub>2</sub>.

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11

Collet, Jurriën W., Thomas R. Roose, Bram Weijers, Bert U. W. Maes, Eelco Ruijter, and Romano V. A. Orru. "Recent Advances in Palladium-Catalyzed Isocyanide Insertions." Molecules 25, no. 21 (2020): 4906. http://dx.doi.org/10.3390/molecules25214906.

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Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose inherent N-substitution allows for the rapid incorporation of nitrogeneous fragments in a wide variety of products. Recent developments in palladium catalyzed isocyanide insertion reactions have significantly expanded the scope and applicability of these imidoylative cross-couplings. This review high

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12

Motaghi, Milad, Hormoz Khosravi, Saeed Balalaie, and Frank Rominger. "Catalytic formal [4 + 1] isocyanide-based cycloaddition: an efficient strategy for the synthesis of 1H-cyclopenta[b]quinolin-1-one derivatives." Organic & Biomolecular Chemistry 17, no. 2 (2019): 275–82. http://dx.doi.org/10.1039/c8ob02857e.

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Herein we describe an unprecedented isocyanide-based cycloaddition of alkyl and aryl isocyanides with (Z)-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes. On the basis of DFT calculations a mechanism is proposed.

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13

Shiri, Morteza, Noushin Farajinia-Lehi, Parvin Salehi, and Zahra Tanbakouchian. "Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry." Synthesis 52, no. 21 (2020): 3162–88. http://dx.doi.org/10.1055/s-0040-1707357.

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AbstractThe synthesis of amides is a substantial research area in organic chemistry because of their ubiquitous presence in natural products and bioactive molecules. The use of easily accessible isocyanides as amidoyl (carbamoyl) synthons in cross-coupling reactions using transition metal and inner transition metöal catalysts is a current trend in this area. Isocyanides, owing to their coordination ability as a ligand and inherent electronic properties for reactions with various partners, have expanded the potential application of these transformations for the preparation of novel synthetic mo

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14

El Kaïm, Laurent, Laurence Grimaud, and Pravin Patil. "Oxazole Synthesis from Isocyanides." Synlett 23, no. 09 (2012): 1361–63. http://dx.doi.org/10.1055/s-0031-1290939.

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15

Heß, Ulrich, Holger Brosig, and Wolf P. Fehlhammer. "Electrochemical synthesis of isocyanides." Tetrahedron Letters 32, no. 40 (1991): 5539–42. http://dx.doi.org/10.1016/0040-4039(91)80078-k.

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16

Katritzky, Alan R., Linghong Xie та Wei-Qiang Fan. "Synthesis of α-Amino Isocyanides and α-Alkylthio Isocyanides". Synthesis 1993, № 01 (1993): 45–47. http://dx.doi.org/10.1055/s-1993-25788.

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17

Ichikawa, Yoshiyasu, Toshiki Yamasaki, Keisuke Nakanishi, Yutaro Udagawa, Seijiro Hosokawa, and Toshiya Masuda. "Bioinspired Synthesis of the Central Core of Halichonadin H: The Passerini Reaction in a Hypothetical Biosynthesis of Marine Natural Products." Synthesis 51, no. 11 (2019): 2305–10. http://dx.doi.org/10.1055/s-0037-1610867.

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A pathway is proposed for the biosynthesis of the unique homodimeric terpene, halichonadin H. The proposed biosynthetic pathway involves two key Passerini reactions of eudesmane-type terpene isocyanides. The Passerini reaction of a model terpene isocyanide and formaldehyde afforded an α-hydroxy acetamide, which was further subjected to oxidation and a second Passerini reaction. This reaction sequence furnished an α-hydroxy malonamide connected with two identical terpene units which is the identical structural motif found in halichonadin H.

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18

Kurup, Sudheer S., Richard J. Staples, Richard L. Lord, and Stanislav Groysman. "Synthesis of Chromium(II) Complexes with Chelating Bis(alkoxide) Ligand and Their Reactions with Organoazides and Diazoalkanes." Molecules 25, no. 2 (2020): 273. http://dx.doi.org/10.3390/molecules25020273.

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Synthesis of new chromium(II) complexes with chelating bis(alkoxide) ligand [OO]Ph (H2[OO]Ph = [1,1′:4′,1′’-terphenyl]-2,2′’-diylbis(diphenylmethanol)) and their subsequent reactivity in the context of catalytic production of carbodiimides from azides and isocyanides are described. Two different Cr(II) complexes are obtained, as a function of the crystallization solvent: mononuclear Cr[OO]Ph(THF)2 (in toluene/THF, THF = tetrahydrofuran) and dinuclear Cr2([OO]Ph)2 (in CH2Cl2/THF). The electronic structure and bonding in Cr[OO]Ph(THF)2 were probed by density functional theory calculations. Isola

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19

Yu, Yang, Yan Zhang, Zhuo Wang, Yong-Xin Liang, and Yu-Long Zhao. "A rhodium-catalyzed three-component reaction of arylisocyanides, trifluorodiazoethane, and activated methylene isocyanides or azomethine ylides: an efficient synthesis of trifluoroethyl-substituted imidazoles." Organic Chemistry Frontiers 6, no. 21 (2019): 3657–62. http://dx.doi.org/10.1039/c9qo00856j.

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A novel method for the synthesis of trifluoroethyl-substituted imidazoles is reported via a rhodium-catalyzed three-component reaction of isocyanides, 2,2,2-trifluorodiazoethane and activated methylene isocyanides or azomethine ylides.

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20

Moderhack, Dietrich. "N-Isocyanides—synthesis and reactions." Tetrahedron 68, no. 30 (2012): 5949–67. http://dx.doi.org/10.1016/j.tet.2012.04.099.

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21

KATRITZKY, A. R., L. XIE та W. Q. FAN. "ChemInform Abstract: Synthesis of α-Amino Isocyanides and α-Alkylthio Isocyanides." ChemInform 24, № 38 (2010): no. http://dx.doi.org/10.1002/chin.199338143.

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22

Suć, Josipa, Danijela Barić, and Ivanka Jerić. "Multicomponent synthesis of hydrazino depsipeptides." RSC Advances 6, no. 102 (2016): 99664–75. http://dx.doi.org/10.1039/c6ra23317a.

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23

Zarezin, Danil P., Olga I. Shmatova та Valentine G. Nenajdenko. "Chiral β3-isocyanopropionates for multicomponent synthesis of peptides and depsipeptides containing a β-amino acid fragment". Organic & Biomolecular Chemistry 16, № 33 (2018): 5987–98. http://dx.doi.org/10.1039/c8ob01507d.

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Chiral β<sub>3</sub>-isocyanopropionic acids derivatives is a new type of isocyanides for multicomponent reactions. The use of these isocyanides in Ugi and Passerini reactions allows to prepare short peptides and depsipeptides with β-amino acid moiety in the structure.

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24

Kaur, Tanpreet, Preeti Wadhwa, and Anuj Sharma. "Arylsulfonylmethyl isocyanides: a novel paradigm in organic synthesis." RSC Advances 5, no. 65 (2015): 52769–87. http://dx.doi.org/10.1039/c5ra07876h.

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p-Tosylmethyl isocyanide (TosMIC), an α-acidic isocyanide has emerged as a privileged reagent to access biologically relevant fused heterocycles and some natural products like (−)-ushikulide A, variolin B, porphobilinogen and mansouramycin B.

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25

Pelliccia, Sveva, Vincenzo Abbate, Fiorella Meneghetti, et al. "On-water pyrrolidine-mediated domino synthesis of 2-iminoisatins." Green Chemistry 20, no. 17 (2018): 3912–15. http://dx.doi.org/10.1039/c8gc01090k.

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26

Waibel, K. A., R. Nickisch, N. Möhl, R. Seim, and M. A. R. Meier. "A more sustainable and highly practicable synthesis of aliphatic isocyanides." Green Chemistry 22, no. 3 (2020): 933–41. http://dx.doi.org/10.1039/c9gc04070f.

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27

Sarnpitak, Pakornwit, and Mikhail Krasavin. "Synthesis of 1,2,4-triazoles employing isocyanides." Tetrahedron 69, no. 10 (2013): 2289–95. http://dx.doi.org/10.1016/j.tet.2013.01.039.

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28

Bauer, Michael, and Uli Kazmaier. "Straightforward Synthesis of Chiral Hydroxy Isocyanides." European Journal of Organic Chemistry 2009, no. 14 (2009): 2360–66. http://dx.doi.org/10.1002/ejoc.200900109.

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29

HESS, U., H. BROSIG, and W. P. FEHLHAMMER. "ChemInform Abstract: Electrochemical Synthesis of Isocyanides." ChemInform 23, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199225122.

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30

El Kaim, Laurent, Laurence Grimaud, and Pravin Patil. "ChemInform Abstract: Oxazole Synthesis from Isocyanides." ChemInform 43, no. 39 (2012): no. http://dx.doi.org/10.1002/chin.201239139.

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31

Campo, J., M. García-Valverde, S. Marcaccini, M. J. Rojo, and T. Torroba. "Synthesis of indole derivatives via isocyanides." Org. Biomol. Chem. 4, no. 5 (2006): 757–65. http://dx.doi.org/10.1039/b514946k.

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32

Tobisu, Mamoru, and Naoto Chatani. "Renaissance of Organic Synthesis Using Isocyanides." Chemistry Letters 40, no. 4 (2011): 330–40. http://dx.doi.org/10.1246/cl.2011.330.

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33

Arshady, Reza, Marco Zecca, and Benedetto Corain. "Polymeric isocyanides: synthesis, properties and applications." Reactive Polymers 20, no. 3 (1993): 147–73. http://dx.doi.org/10.1016/0923-1137(93)90090-3.

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34

van Leusen, Albert M., Jurjen Wildeman, Janusz Moskal, and Anton W. van Hemert. "Synthesis of 1-(arylthio)alkenyl isocyanides." Recueil des Travaux Chimiques des Pays-Bas 104, no. 6 (2010): 177–83. http://dx.doi.org/10.1002/recl.19851040606.

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35

Ma, Yiyang, Zhiyuan Yan, Changliang Bian та ін. "Synthesis of oxazoles by silver catalysed oxidative decarboxylation–cyclization of α-oxocarboxylates and isocyanides". Chemical Communications 51, № 52 (2015): 10524–27. http://dx.doi.org/10.1039/c5cc02253c.

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36

Fini, Francesco, Alessandro Zanni, Maria Luisa Introvigne, Mattia Stucchi, Emilia Caselli та Fabio Prati. "Straightforward synthesis of chiral non-racemic α-boryl isocyanides". Organic & Biomolecular Chemistry 19, № 30 (2021): 6687–91. http://dx.doi.org/10.1039/d1ob00616a.

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37

Jiang, Shuai, Wen-Bin Cao, Hai-Yan Li, Xiao-Ping Xu, and Shun-Jun Ji. "Convenient synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides by cobalt catalysis in pure water." Green Chemistry 23, no. 7 (2021): 2619–23. http://dx.doi.org/10.1039/d1gc00270h.

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38

Krüger, M., H. Dreizler, D. Lentz, and D. Preugschat. "Synthesis and Microwave Spectroscopic Study of Fluorinated Methyl Isocyanides." Zeitschrift für Naturforschung A 49, no. 6 (1994): 703–8. http://dx.doi.org/10.1515/zna-1994-0608.

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Abstract Difluoromethyl isocyanide has been generated by flash vacuum pyrolysis of pentacarbonyl (di-fluoromethyl isocyanide) chromium at 240 °C. Spectroscopic studies revealed the presence of several major and minor impurities like HCN, HCC -CN and HCC -NC . The pyrolysis of pentacarbonyl (fluoromethyl isocyanide)chromium did not lead to the observation of free fluoromethyl isocyanide. The rotational spectrum of difluoromethyl isocyanide has been recorded with a conventional continuous wave Stark spectrometer and a molecular beam Fourier transform microwave spectrometer resulting in A = 10.11

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39

Liu, Jie, Chao Fan, Hongyu Yin та ін. "Synthesis of 6-acyl phenanthridines by oxidative radical decarboxylation–cyclization of α-oxocarboxylates and isocyanides". Chem. Commun. 50, № 17 (2014): 2145–47. http://dx.doi.org/10.1039/c3cc49026b.

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40

Tafuku, Sayaka, Takuya Fukuda, Kazuhiro Chiba, and Yoshikazu Kitano. "A New Method for the Preparation of Bis(alkylamino)maleonitriles from Aliphatic Isocyanides with TMSCN and Bi(OTf)3." Synthesis 51, no. 11 (2019): 2318–22. http://dx.doi.org/10.1055/s-0037-1610865.

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Bis(alkylamino)maleonitriles are starting materials for the synthesis of a number of important intermediates, including porphyrazines that serve as dyes, pigments, and models of biologically active substances; hence, the development of improved methods for their preparation is important. Herein, we report a facile new method for the preparation of bis(alkylamino)maleonitriles from isocyanides. Treatment of tert-alkyl isocyanides with trimethylsilyl cyanide (TMSCN) and trimethylsilyl triflate (TMSOTf) in the presence of bismuth(III) triflate [Bi(OTf)3] afforded the corresponding bis(alkylamino)

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41

Bornadiego, Ana, Jesús Díaz, and Carlos F. Marcos. "Tandem synthesis of 4-aminoxanthones is controlled by a water-assisted tautomerization: a general straightforward reaction." Organic & Biomolecular Chemistry 17, no. 6 (2019): 1410–22. http://dx.doi.org/10.1039/c8ob02527d.

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42

Sadjadi, Samahe, Majid M. Heravi, and Niousha Nazari. "Isocyanide-based multicomponent reactions in the synthesis of heterocycles." RSC Advances 6, no. 58 (2016): 53203–72. http://dx.doi.org/10.1039/c6ra02143c.

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In this review, we update our previous presentation, underscoring the recent applications of isocyanides as privileged synthons in the synthesis of various heterocyclic compounds, especially focused on those synthesizedviamulticomponent reactions.

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43

Németh, András Gy, and Péter Ábrányi-Balogh. "Recent Advances in the Synthesis of Isothiocyanates Using Elemental Sulfur." Catalysts 11, no. 9 (2021): 1081. http://dx.doi.org/10.3390/catal11091081.

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Isothiocyanates (ITCs) are biologically active molecules found in several natural products and pharmaceutical ingredients. Moreover, due to their high and versatile reactivity, they are widely used as intermediates in organic synthesis. This review considers the best practices for the synthesis of ITCs using elemental sulfur, highlighting recent developments. First, we summarize the in situ generation of thiocarbonyl surrogates followed by their transformation in the presence of primary amines leading to ITCs. Second, carbenes and amines afford isocyanides, and the further reaction of this spe

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44

Gu, Zheng-Yang, Hui Han, Zi-Yin Li, Shun-Jun Ji, and Ji-Bao Xia. "Catalytic synthesis of functionalized amidines via cobalt-carbene radical coupling with isocyanides and amines." Organic Chemistry Frontiers 8, no. 7 (2021): 1544–50. http://dx.doi.org/10.1039/d1qo00063b.

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45

Li, Ming, Bin Qiu, Xiang-Jing Kong, and Li-Rong Wen. "Synthesis of Passerini adducts from aldehydes and isocyanides under the auxiliary of water." Organic Chemistry Frontiers 2, no. 10 (2015): 1326–33. http://dx.doi.org/10.1039/c5qo00202h.

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46

Wang, Bo, Dan He, Beige Ren, and Tuanli Yao. "Synthesis of imides via palladium-catalyzed three-component coupling of aryl halides, isocyanides and carboxylic acids." Chemical Communications 56, no. 6 (2020): 900–903. http://dx.doi.org/10.1039/c9cc08438j.

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47

Zhu, Fengxiang, and Xiao-Feng Wu. "Palladium-catalyzed construction of amidines from arylsilanes in the absence of a ligand under oxidative conditions." New Journal of Chemistry 42, no. 12 (2018): 10396–99. http://dx.doi.org/10.1039/c8nj01883a.

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48

Huang, Jie, Feng Li, Lei Cui, Shikuan Su, Xueshun Jia, and Jian Li. "Palladium-catalyzed cascade reactions of enynones and isocyanides: access towards functionalized ketenimine and its application." Chemical Communications 56, no. 33 (2020): 4555–58. http://dx.doi.org/10.1039/c9cc09363j.

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49

Dukanya, Dukanya, Toreshettahally R. Swaroop, Shobith Rangappa, Kanchugarakoppal S. Rangappa, and Basappa Basappa. "Cyclization of Activated Methylene Isocyanides with Methyl N(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1H-imidazol-5-amines." SynOpen 03, no. 03 (2019): 71–76. http://dx.doi.org/10.1055/s-0039-1690328.

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Base-induced cyclization of active methylene isocyanides with carbamimidothioates for the synthesis of N,1-aryl-4-tosyl/ethylcarboxy-1H-imidazol-5-amines is reported. The diversity of the reactions is exemplified by using various carbamimidothioates obtained from symmetrical N,N-disubstituted, unsymmetrical N,N,N-trisubstituted, and unsymmetrical N,N-disubstituted thioureas. This diversity is further enriched by different isocyanides. A mechanism for the formation of the title compounds is proposed.

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50

Hu, Zhongyan, Mingyue Zhang, Qinghua Zhou, Xianxiu Xu, and Bo Tang. "Domino synthesis of fully substituted pyridines by silver-catalyzed chemoselective hetero-dimerization of isocyanides." Organic Chemistry Frontiers 7, no. 3 (2020): 507–12. http://dx.doi.org/10.1039/c9qo01333d.

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A silver-catalyzed hetero-dimerization of various vinyl isocyanides with isocyanoacetamides has been developed for the efficient and practical synthesis of fully substituted pyridines in a single operation.

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