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Journal articles on the topic 'Imines – Synthèse'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Maroni, Pierre, Yves Madaule, Tula Seminario, and Jean-Gérard Wolf. "Hétérocycles organiques de l'arsenic. Synthèse d'arsinimines hétérocycliques par la "réaction de Staudinger." Mécanisme de la réaction." Canadian Journal of Chemistry 63, no. 3 (1985): 636–42. http://dx.doi.org/10.1139/v85-104.

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Staudinger's reaction is applied on arsenic hétérocycles. Picryl and tosyl azides lead, by action on tetracoordinated arsatranes, to previously unknown pentacoordinated arsinimines with an "atran" bond (N → As). In a second step, they dimerize to diarsadiazacyclobutanes, bearing hexacoordinated arsenic atoms. Heterocyclic arsanes react only with picryl azide. All imines were obtained as dimers or oligomers, with the single exception of 8A. Ultraviolet studies give evidence for an intermediate complex different from the one demonstrated in the "classical" Staudinger's reaction with phosphorus compounds.

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2

Mendes, Joseane A., Paulo R. R. Costa, Miguel Yus, Francisco Foubelo, and Camilla D. Buarque. "N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles." Beilstein Journal of Organic Chemistry 17 (May 12, 2021): 1096–140. http://dx.doi.org/10.3762/bjoc.17.86.

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The synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from tert-butanesulfinamide. These imines are versatile chiral auxiliaries and have been extensively used as eletrophiles in a wide range of reactions. The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the tert-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles. The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral N-tert-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products. The synthesis of nitrogen-containing heterocycles in which the nitrogen atom is not provided by the chiral imine will not be considered in this review. The sections are organized according to the size of the heterocycles. The present work will comprehensively cover the most pertinent contributions to this research area from 2012 to 2020. We regret in advance that some contributions are excluded in order to maintain a concise format.

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3

Rivière-Baudet, M., P. Rivière, J. Satgé та G. Lacrampe. "Petits cycles à liaison germanium-azote: Synthèse et réactivité de germa-2 azolidines, germa-2 azétidines, germa-2 aziridines. Caractérisation de germa-imines: Nouveaux intermédiaires à germanium π-lié". Recueil des Travaux Chimiques des Pays-Bas 98, № 2 (2010): 42–52. http://dx.doi.org/10.1002/recl.19790980205.

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4

Ren, Ren, and Jiantai Ma. "Lamellar Ni/Al-SBA-15 fibers: preparation, characterization, and applications as highly efficient catalysts for amine and imine syntheses." RSC Advances 5, no. 91 (2015): 74802–10. http://dx.doi.org/10.1039/c5ra14382a.

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5

Cai, Sen-Lin, Bin-Hua Yuan, Yi-Xiang Jiang, Guo-Qiang Lin, and Xing-Wen Sun. "Asymmetric cinnamylation of N-tert-butanesulfinyl imines with cinnamyl acetates: total syntheses of (+)-lycoricidine and (+)-7-deoxypancratistatin." Chemical Communications 53, no. 25 (2017): 3520–23. http://dx.doi.org/10.1039/c7cc00108h.

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Total syntheses of (+)-lycoricidine and (+)-7-deoxypancratistatin have been achieved through highly diastereoselective palladium-catalyzed cinnamylation of N-tert-butanesulfinyl imines with cinnamyl acetates.

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6

Cazaux, Louis, Mourad Faher, Claude Picard, and Pierre Tisnès. "Styrylbenzodiazinones 1. Synthèse, structure et propriétés photophysiques." Canadian Journal of Chemistry 71, no. 12 (1993): 2007–15. http://dx.doi.org/10.1139/v93-250.

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Several 3-styryl derivatives of 1,4-benzodiazine-2-one and of 1-methyl-1,4-benzodiazine-2-one were prepared. A structural study of these compounds by 1H and 13C NMR and by molecular modelling was carried out. The rotational isomerism around the bond connecting the imine and vinyl groups in these E styrylbenzodiazinones is discussed. The s-cis rotamer is shown to be the predominant isomer. The photophysical properties of these fluorescent dyes are reported.

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7

Shankaran, K., Karla L. Donnelly, Shrenik K. Shah, et al. "Evaluation of pyrrolidin-2-imines and 1,3-thiazolidin-2-imines as inhibitors of nitric oxide synthase." Bioorganic & Medicinal Chemistry Letters 14, no. 17 (2004): 4539–44. http://dx.doi.org/10.1016/j.bmcl.2004.06.033.

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8

Bai, Yüniu, Mathias Noltemeyer, and Herbert W. Roesky. "Synthese und Strukturen von Monoalkylamiden und -imiden des Titans / Synthesis and Structures of Monoalkylamides and -imides of Titanium." Zeitschrift für Naturforschung B 46, no. 10 (1991): 1357–63. http://dx.doi.org/10.1515/znb-1991-1014.

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A new method for the preparation of monoalkylamides of composition Cp′TiCl2NHR is reported. Me3SnNHR (R = tBu 1a, CHiPr2 1b) reacts with Cp′TiCl3 with elimination of Me3SnCl to yield Cp′TiCl2NHR (2) (2a: Cp′ = C5H5, R = tBu, 2b: Cp′ = Me3SiC5H4, R = tBu, 2c: Cp′ = (Me3Si)2C5H3, R = tBu, 2d: Cp′ = Me4C5H, R = tBu, 2e: Cp′ = Me5C5, R = tBu, 2f: Cp′ = C5H5, R = CHiPr2, 2g: Cp′ = Me3SiC5H4, R = CHiPr2, 2h: Cp′ = (Me3Si)2C5H3, R = CHiPr2, 2i: Cp′ = Me4C5H, R = CHiPr2, 2j: Cp′ = Me5C5, R = CHiPr2). Compounds 2a-2j are stable and eliminate HCl only in the presence of a strong base to form (C5H5TiClNtBu)2 (3a) or (Me3SiC5H4TiClNtBu)2 (3b) from 2a and 2b, respectively. In 3a the chlorine atoms are substituted by NHtBu groups in boiling THF by means of LiNHtBu to give (C5H5TiNHtBuNtBu)2 (4). The reactions of 2e and 2b with LiN(SiMe3)2·Et2O in the presence of pyridine yield Me5C5TiClNtBu · Py (5a) (Py = pyridine) and Me3SiC5H4TiClNtBu·Py (5b), respectively. Compounds 2e and 5a have been characterized by X-ray crystal structural analysis.

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9

Ramachandran, P. Veeraraghavan, and Thomas E. Burghardt. "Recent developments in the chiral synthesis of homoallylic amines via organoboranes." Pure and Applied Chemistry 78, no. 7 (2006): 1397–406. http://dx.doi.org/10.1351/pac200678071397.

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Among the plethora of protocols for the preparation of chiral homoallylic amines, the use of boron-based reagents remains relatively undeveloped. However, the recent advances in the use of α-pinene-based versatile reagents for the synthesis of such amines confirmed that very high enantioselectivity and outstanding diastereoselectivity can be readily achieved. Addition of the "allyl"boron reagents to various N-substituted imines provided the desired amine products in high yields and high to very high ee. The discovery that an addition of 1.0 equiv of methanol or water to the "allyl"boration reaction with N-masked imines is critical allowed for higher yields and noticeably improved ee. The use of N-aluminoimines, which are not only easy to prepare by a partial reduction of nitriles, but are also relatively stable for both enolizable and non-enolizable substrates, considerably expanded the scope of the reactions. In this review, the developments in the syntheses of chiral homoallylic amines using organoboranes, with the particular accent on the reagent-controlled reactions, are summarized. Additionally, the novel methodology for the crotyl- and alkoxyallylboration of imines using trialkylboron "ate" complexes is described.

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10

Borthwick, Emma B., Susanne J. Connell, David W. Tudor, et al. "Escherichia coli dihydrodipicolinate synthase: characterization of the imine intermediate and the product of bromopyruvate treatment by electrospray mass spectrometry." Biochemical Journal 305, no. 2 (1995): 521–24. http://dx.doi.org/10.1042/bj3050521.

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Simplified procedures for assaying and purifying dihydrodipicolinate synthase (EC 4.2.1.52), the first enzyme of the lysine biosynthetic pathway, have been developed and electrospray ionization m.s. has been used to observe the imine intermediate with pyruvate and to investigate the reaction of the enzyme with bromopyruvate and fluoropyruvate.

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11

Sathish, Manda, Fabiane M. Nachtigall та Leonardo S. Santos. "Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (−)-coerulescine and (−)-horsfiline by oxidative rearrangement". RSC Advances 10, № 63 (2020): 38672–77. http://dx.doi.org/10.1039/d0ra07705d.

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A simple and efficient asymmetric synthesis of THBCs through a chiral thiosquaramide 11b catalyzed imine reduction of dihydro-β-carbolines (17a−f) and syntheses of (−)-coerulescine and (–)-horsfiline via enantioselective oxidative rearrangement.

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12

Dragone, Vincenza, Victor Sans, Mali H. Rosnes, Philip J. Kitson, and Leroy Cronin. "3D-printed devices for continuous-flow organic chemistry." Beilstein Journal of Organic Chemistry 9 (May 16, 2013): 951–59. http://dx.doi.org/10.3762/bjoc.9.109.

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We present a study in which the versatility of 3D-printing is combined with the processing advantages of flow chemistry for the synthesis of organic compounds. Robust and inexpensive 3D-printed reactionware devices are easily connected using standard fittings resulting in complex, custom-made flow systems, including multiple reactors in a series with in-line, real-time analysis using an ATR-IR flow cell. As a proof of concept, we utilized two types of organic reactions, imine syntheses and imine reductions, to show how different reactor configurations and substrates give different products.

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13

Migneault, David, Michael A. Bernstein, and Cheuk K. Lau. "Preparation of ortho-hydroxyalkylanilines as ortho-quinone methide imine precursors via an aminoborane complex." Canadian Journal of Chemistry 73, no. 9 (1995): 1506–13. http://dx.doi.org/10.1139/v95-186.

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A general process for ortho-specific hydroxyalkylation of secondary anilines has been developed. N-Methylanilinochlorophenylboranes react readily with aryl aldehydes, and with α,β-unsaturated or saturated aliphatic aldehydes to give the corresponding ortho-hydroxyalkylanilines in good yield. Thermolysis of the latter generated the corresponding ortho-quinone methide imine, which can participate in an electrocyclic or intramolecular [4 + 2] cycloaddition reaction to give various dihydro- and tetrahydroquinoline derivatives. Application of the method to the syntheses of 5-aza analogs of hexahydrocannabinol is demonstrated. Keywords: quinone methide imine, ortho-hydroxyalkylaniline, azacannabinoids.

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14

Barion, Detlef, Gabriele David, Manfred Link, Martin Nieger, and Edgar Niecke. "Synthese und Struktur von Phosphiren-Iminen und Iminophosphaspiro[2.2]pentanen." Chemische Berichte 126, no. 3 (1993): 649–55. http://dx.doi.org/10.1002/cber.19931260315.

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15

Kawanaka, Yasufumi, Kaoru Kobayashi, Shinya Kusuda, et al. "One Step Synthesis of Dihydropyridin-2-imines: Inhibitors of Inducible Nitric Oxide Synthase." Synlett, no. 8 (2002): 1233–36. http://dx.doi.org/10.1055/s-2002-32982.

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16

Jüschke, Ralf, Gerald Henkel, and Peter Sartori. "Synthese und Struktur von Kalium-4,4-difluor-[1,3,2]dithiazetidinid-1,l,3,3-tetraoxid und Rubidium-4,4,5,5-tetrafluor-[1,3,2]dithiazolidinid-1,1,3,3-tetraoxid / Syntheses and Structure of Potassium-4,4-difluoro-[1,3,2]dithiazetidinide-1,1,3,3- tetraoxide and Rubidium-4,4,5,5-tetrafluoro-[ 1,3,2]dithiazolidinide-1,1,3,3-tetraoxide." Zeitschrift für Naturforschung B 52, no. 3 (1997): 359–66. http://dx.doi.org/10.1515/znb-1997-0311.

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Abstract Reactions of perfluoroalkane-1,n-bis(sulfonylfluorides) (n = 1-2) (1-2) with liquid ammonia in tetrahydrofuran (TH F) lead to the cyclic ammonium imides 3-4. These cyclic imides 3-4 can easily be transform ed to other salts using the corresponding hydroxides. X -ray structure analyses (T = 150 K) were perform ed for the potassium 4,4-difluoro-[1,3,2]dithiazetidinide-1,1,3,3-tetraoxide 5 and rubidium -4,4,5,5-tetrafluoro-[1,3,2]dithiazolidinide-1,1,3,3-tetraoxide 6. Cylic imides of the type 3, 5 have not been reported previously. Their formation and their nmr-data are discussed.

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17

Brunner, Henri, Markus Niemetz, and Manfred Zabel. "Optisch aktive Übergangsmetall-Komplexe, 122. Synthese von Palladium(II)-Schiff-Base-Komplexen -intramolekulare Wechselwirkungen / Optically Active Transition Metal Complexes, 122. Synthesis of Palladium (II) Complexes with Schiff Base Ligands -Intramolecular Interactions." Zeitschrift für Naturforschung B 55, no. 2 (2000): 145–54. http://dx.doi.org/10.1515/znb-2000-0203.

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Abstract Imines of salicylaldehyde and 2,6-diformyl-p-cresol have been used as ligands in palladium (II) complexes. Enantiomerically pure ligands give enantiomerically pure complexes, racemic ligands give racemates and meso-forms. Differences between the respective isomers of the ligands within the complexes and between the diastereomers of the complexes were investigated. Crystal structure analyses established the trans configuration at the metal center.

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18

Hansen, Karl B., Nathaniel S. Finney, and Eric N. Jacobsen. "Carbenoidübertragung auf Imine: eine neue asymmetrische katalytische Synthese von Aziridinen." Angewandte Chemie 107, no. 6 (1995): 750–52. http://dx.doi.org/10.1002/ange.19951070626.

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19

Reeksting, Shaun B., Ingrid B. Müller, Pieter B. Burger, et al. "Exploring inhibition of Pdx1, a component of the PLP synthase complex of the human malaria parasite Plasmodium falciparum." Biochemical Journal 449, no. 1 (2012): 175–87. http://dx.doi.org/10.1042/bj20120925.

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Malaria tropica is a devastating infectious disease caused by Plasmodium falciparum. This parasite synthesizes vitamin B6de novo via the PLP (pyridoxal 5′-phosphate) synthase enzymatic complex consisting of PfPdx1 and PfPdx2 proteins. Biosynthesis of PLP is largely performed by PfPdx1, ammonia provided by PfPdx2 subunits is condensed together with R5P (D-ribose 5-phosphate) and G3P (DL-glyceraldehyde 3-phosphate). PfPdx1 accommodates both the R5P and G3P substrates and intricately co-ordinates the reaction mechanism, which is composed of a series of imine bond formations, leading to the production of PLP. We demonstrate that E4P (D-erythrose 4-phosphate) inhibits PfPdx1 in a dose-dependent manner. We propose that the acyclic phospho-sugar E4P, with a C1 aldehyde group similar to acyclic R5P, could interfere with R5P imine bond formations in the PfPdx1 reaction mechanism. Molecular docking and subsequent screening identified the E4P hydrazide analogue 4PEHz (4-phospho-D-erythronhydrazide), which selectively inhibited PfPdx1 with an IC50 of 43 μM. PfPdx1 contained in the heteromeric PLP synthase complex was shown to be more sensitive to 4PEHz and was inhibited with an IC50 of 16 μM. Moreover, the compound had an IC50 value of 10 μM against cultured P. falciparum intraerythrocytic parasites. To analyse further the selectivity of 4PEHz, transgenic cell lines overexpressing PfPdx1 and PfPdx2 showed that additional copies of the protein complex conferred protection against 4PEHz, indicating that the PLP synthase is directly affected by 4PEHz in vivo. These PfPdx1 inhibitors represent novel lead scaffolds which are capable of targeting PLP biosynthesis, and we propose this as a viable strategy for the development of new therapeutics against malaria.

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20

Dehne, Heinz, and Veronika Maaβ. "Synthese von 3-Aryl-4-(phenoxathiin-2-yl)thiazolin-2-iminen." Zeitschrift für Chemie 28, no. 8 (2010): 296. http://dx.doi.org/10.1002/zfch.19880280816.

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21

Geffken, Detlef. "Synthese und Eigenschaften von 3-Alkoxy(hydroxy)thiazolidin-2,4-dionen / Synthesis and Properties of 3-Alkoxy(hydroxy)thiazolidin-2,4-diones." Zeitschrift für Naturforschung B 42, no. 9 (1987): 1202–6. http://dx.doi.org/10.1515/znb-1987-0923.

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The reaction of 2-mercaptocarboxylic acids (3 B ) or methyl thioglycolates (3 A ) with 1.1'-carbonyldiimidazole and alkoxyamines produces 3-alkoxythiazolidin-2,4-diones (5). Acid catalyzed methanolysis of the tetrahydropyranyloxy group affords the cyclic N-hydroxy imides (6) which can easily be acylated with 3-chlorophenylisocyanate or dimethylcarbamoyl chloride to give compounds of type 7 or 8.

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22

Martin, Stephen F. "Recent applications of imines as key intermediates in the synthesis of alkaloids and novel nitrogen heterocycles." Pure and Applied Chemistry 81, no. 2 (2009): 195–204. http://dx.doi.org/10.1351/pac-con-08-07-03.

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One of the major challenges in contemporary synthetic organic chemistry is the design and development of new tactics and strategies and their application to concise and efficient syntheses of biologically active natural products. Strategies that utilize reactions that enable the rapid assembly of the skeletal framework of such targets are thus especially attractive. In this context, we have developed novel applications of imine chemistry in Mannich and related reactions, cascade processes, and multicomponent reactions (MCRs) to rapidly assemble structural subunits common to diverse families of alkaloids. The practical utility of these chemistries is evidenced by their use in the execution of facile total syntheses of (±)-epilupinine (1), (±)-tashiromine (2), (-)-epimyrtine (3), and (±)-roelactamine (4) as well as other nitrogen heterocycles of potential biological interest.

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23

Kawanaka, Yasufumi, and et al et al. "ChemInform Abstract: One-Step Synthesis of Dihydropyridine-2-imines. Inhibitors of Inducible Nitric Oxide Synthase." ChemInform 33, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.200245117.

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24

Kantlehner, Willi, Jochen Mezger, Ioannis Tiritiris, Ralf Kreß, and Wolfgang Frey. "Orthoamide und Iminiumsalze, CIII. Synthese von N,N′,N′′-peralkylierten Guanidiniumsalz-basierten ionischen Flüssigkeiten durch Anionenmetathese." Zeitschrift für Naturforschung B 76, no. 2 (2021): 133–62. http://dx.doi.org/10.1515/znb-2020-0074.

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Abstract N,N′,N′′-peralkylated guanidinium chlorides and N,N′,N′′-peralkylated guanidines were prepared from N,N′-peralkylated chloroformamidinium chlorides. The alkylation of the guanidines affords N,N′,N′′-persubstituted guanidinium chlorides bromides, iodides, alkylsulfates, and tetrafluoroborates. Guanidinium tricyanomethanides and tetracyanopropenides were prepared from the chlorides and iodides by anion metathesis. The reaction of guanidinium halogenides with borontrifluoride etherate, triethyloxonium tetrafluoroborate or sodiumtetrafluoroborate delivers guanidinium tetrafluoroborates. Guanidinium saccharinides, cyanates, thiocyanates, trifluoromethansulfonates, bis(trifluormethansulfonyl)imides, hexacyanoferrates(II/III), tetracyanonickolates and tetrathiocyanatocobaltates were prepared from the corresponding guanidinium chlorides and tetrafluoroborates by anion exchange.

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25

Shi, Zhuangzhi, and Frank Glorius. "Effiziente und vielseitige Indol-Synthese aus Enaminen und Iminen mithilfe dehydrierender Kreuzkupplung." Angewandte Chemie 124, no. 37 (2012): 9354–56. http://dx.doi.org/10.1002/ange.201205079.

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26

Oueslati, Ahmed, Hatem Ben Romdhane, Régis Mercier, and Refaât M. Chaâbouni. "Synthèse et propriétés photochimiques de modèles imides et amides contenant des structures norbornadiènes pentaméthylés." Comptes Rendus Chimie 13, no. 11 (2010): 1406–15. http://dx.doi.org/10.1016/j.crci.2010.04.025.

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27

Koch, Thomas, Vassil I. Ognyanov, and Manfred Hesse. "Synthese von Makrocyclen durch Ringerweiterung von 14gliedrigen cyclischen Imiden." Helvetica Chimica Acta 75, no. 1 (1992): 62–68. http://dx.doi.org/10.1002/hlca.19920750104.

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28

Itsuno, Shinichi, Katsuhiro Watanabe, Koichi Ito, Ashraf A. El-Shehawy, and Ali A. Sarhan. "Enantioselektive Synthese von Homoallylaminen durch nucleophile Addition von chiralen Allylborreagentien an Imine." Angewandte Chemie 109, no. 1-2 (1997): 105–7. http://dx.doi.org/10.1002/ange.19971090131.

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29

Wakchaure, Vijay N., and Benjamin List. "Katalytische asymmetrische reduktive Kondensation von N-H-Iminen: Synthese vonC2-symmetrischen sekundären Aminen." Angewandte Chemie 128, no. 51 (2016): 16007–10. http://dx.doi.org/10.1002/ange.201608329.

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30

Arend, Michael, та Nikolaus Risch. "Regio- und diastereoselektive Synthese von β-Aminoketonen durch Addition von Iminen an Iminiumsalze". Angewandte Chemie 107, № 23-24 (1995): 2861–62. http://dx.doi.org/10.1002/ange.19951072308.

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31

Zhou, Shaolin, Steffen Fleischer, Kathrin Junge, Shoubhik Das, Daniele Addis, and Matthias Beller. "Asymmetrische Synthese von Aminen: eine allgemeine und effiziente eisenkatalysierte enantioselektive Transferhydrierung von Iminen." Angewandte Chemie 122, no. 44 (2010): 8298–302. http://dx.doi.org/10.1002/ange.201002456.

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32

Roesky, Herbert W., Andrew May, and Mathias Noltemeyer. "Synthese von Heterocyclen durch Verwendung von Bis(trifluormethyl)sulfin-imiden." Journal of Fluorine Chemistry 62, no. 1 (1993): 77–99. http://dx.doi.org/10.1016/s0022-1139(00)80083-4.

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33

Kawanaka, Yasufumi, Kaoru Kobayashi, Shinya Kusuda, et al. "Design and synthesis of orally bioavailable inhibitors of inducible nitric oxide synthase. synthesis and biological evaluation of dihydropyridin-2(1H)-imines and 1,5,6,7-Tetrahydro-2H-azepin-2-imines." Bioorganic & Medicinal Chemistry 11, no. 5 (2003): 689–702. http://dx.doi.org/10.1016/s0968-0896(02)00540-0.

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34

Liebscher, Jürgen, and Yohannes Fororo Kelboro. "Über Nitril-Formamidchlorid-Addukte; Synthese und Abwandlung von 2-Azatrimethiniumsalzen zu Pyrimidin-4-iminen." Zeitschrift für Chemie 29, no. 5 (2010): 170–72. http://dx.doi.org/10.1002/zfch.19890290508.

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35

Dar’in, Dmitry, Mikhail Krasavin, Anton V. Budeev, and Grigory Kantin. "Continued Exploration of Trifunctional Alkyl 4-Chloro-2-diazo-3-oxobutanoates: Streamlined Entry into [1,2,3]Triazolo[5,1-c][1,4]benzoxazines and [1,2,3]Triazolo[5,1-c][1,4]benzoxazepines." Synthesis 53, no. 12 (2021): 2155–66. http://dx.doi.org/10.1055/a-1348-9031.

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AbstractFurther exploration of the trifunctional character of previously introduced alkyl 4-chloro-2-diazo-3-oxobutanoates in reactions with N-protected substituted o-aminophenols followed by deprotection provided a convenient entry into [1,2,3]triazolo[5,1-c][1,4]benzoxazines, which are of high medicinal importance, as documented in the literature. The same approach applied to N-protected substituted o-(aminomethyl)phenols afforded [1,2,3]triazolo[5,1-c][1,4]benzoxazepines, which are practically unexplored compounds from a medicinal chemistry perspective. The syntheses start with SN2-type alkylation of the phenol. Removal of the protecting group triggers imine formation followed by Wolff 1,2,3-triazole synthesis.

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36

Wagler, Jörg, Thomas Doert, and Gerhard Roewer. "Synthese von Aminen aus Iminen in der Koordinationssphäre von Silicium– eineüberraschende Photoumlagerung von hexakoordinierten Organosilanen." Angewandte Chemie 116, no. 18 (2004): 2495–98. http://dx.doi.org/10.1002/ange.200353267.

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37

Ye, Jian‐Heng, Peter Bellotti, Tiffany O. Paulisch, Constantin G. Daniliuc та Frank Glorius. "Durch sichtbares Licht vermittelte Cycloadditionen von α‐Ketoacylsilanen mit Iminen: Einfache Synthese von β‐Lactamen". Angewandte Chemie 133, № 24 (2021): 13785–90. http://dx.doi.org/10.1002/ange.202102451.

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38

Janowski, Robert, Georgia Kefala, and Manfred S. Weiss. "The structure of dihydrodipicolinate reductase (DapB) fromMycobacterium tuberculosisin three crystal forms." Acta Crystallographica Section D Biological Crystallography 66, no. 1 (2009): 61–72. http://dx.doi.org/10.1107/s0907444909043960.

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Dihydrodipicolinate reductase (DHDPR, DapB) is an enzyme that belongs to the L-lysine biosynthetic pathway. DHDPR reduces the α,β-unsaturated cyclic imine 2,3-dihydrodipicolinic acid to yield the compound 2,3,4,5-tetrahydrodipicolinic acid in a pyridine nucleotide-dependent reaction. The substrate of this reaction is the unstable product of the preceding enzyme dihydrodipicolinate synthase (DHDPS, DapA). Here, the structure of apo-DHDPR fromMycobacterium tuberculosisis reported in two orthorhombic crystal forms, as well as the structure of DHDPR fromM. tuberculosisin complex with NADH in a monoclinic crystal form. A comparison of the results with previously solved structures of this enzyme shows that DHDPR undergoes a major conformational change upon binding of its cofactor. This conformational change can be interpreted as one of the low-frequency normal modes of the structure.

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39

Calow, Adam D. J., Elena Fernández, and Andrew Whiting. "Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach." Org. Biomol. Chem. 12, no. 32 (2014): 6121–27. http://dx.doi.org/10.1039/c4ob01142b.

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40

Luong Xuan, Dien. "Syntheses and Characterizations of Platinum Complexes with New Pyrene-based Salicylaldiminato-type Ligand Substituted at 7-Position of Pyrene." Vietnam Journal of Catalysis and Adsorption 10, no. 2 (2021): 26–35. http://dx.doi.org/10.51316/jca.2021.024.

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Many experimental data show that bulky substituents on the molecules enhance solubility, catalytic activity, and photophysical properties due to the prevention of π-π stacking in metal salicylaldimines. In order to understand the effect of bulkiness of substituents on the properties of the obtained molecules, the author researched and synthesized two new pyrene-based salicylaldiminato-type ligands that were substituted at 7-position and functionalized on imine group with bulky substituents. After the introduction of the tert-butyl group at 7-position of pyrene by Friedel-Crafts reaction, the syntheses of new ligands 1-hydroxy-2-[((2,6-dimethylphenyl)-imino)methyl]-7-(tert-butyl)-pyrene 3, 2-hydroxy-1- [((2,6-dimethylphenyl)imino)methyl]-7-(tert-butyl)-pyrene 4 and corresponding platinum complexes 3(Pt), 4(Pt) were performed in the different ways with the synthetic processes of the complexes 1(Pt) and 2(Pt). The new ligands and complexes were characterized by 1H NMR, IR spectroscopy, mass spectroscopy, elemental analysis and X-ray diffraction, only for 3(Pt). In addition to measurements of the absorption and emission spectra, TDDFT calculations using the B3LYP functions were also performed. The complexes 3(Pt) and 4(Pt) exhibit good solubility and red-shift in absorption and emission spectra because of tert-butyl group at 7-position of pyrene and extension of the delocalized π-orbitals to the 2,6-dimethylphenyl on imine group. The change of functional groups also induces the upfield shift of the protons affected by ring currents of phenyl groups Ar-3, Ar-4 on imine groups. Introduction of t-butyl groups in pyrene moieties can stabilize radical forms in oxidation processes.

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41

Bai, Yüniu, Herbert W. Roesky, Mathias Noltemeyer, and Michael Witt. "Synthese und Strukturen von (Monoorganyl)amiden und -imiden des Zirkoniums und Hafniums." Chemische Berichte 125, no. 4 (1992): 825–31. http://dx.doi.org/10.1002/cber.19921250411.

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42

Renson, M., and R. Collienne. "Synthèse de Thio- et Séléno-Phtalides À Partir des Esters Imides Cycliques Correspondants ou de Leur Forme Tautomère." Bulletin des Sociétés Chimiques Belges 73, no. 5-6 (2010): 491–506. http://dx.doi.org/10.1002/bscb.19640730517.

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Kawanaka, Yasufumi, Kaoru Kobayashi, Shinya Kusuda, et al. "Design and Synthesis of Orally Bioavailable Inhibitors of Inducible Nitric Oxide Synthase. Identification of 2-Azabicyclo[4.1.0]heptan-3-imines." Bioorganic & Medicinal Chemistry 11, no. 8 (2003): 1723–43. http://dx.doi.org/10.1016/s0968-0896(03)00034-8.

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44

Hé-Line Wai Tan, Wai, Catherine Bourdieu та André Foucaud. "Reactions de la dichlorophenylphosphine avec les imines : synthese des dihydro-1,2 λ3-azaphosphinines-1,2 et des OXO-2 azaphospholenes-1,2,4". Tetrahedron 46, № 19 (1990): 6715–30. http://dx.doi.org/10.1016/s0040-4020(01)87861-3.

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45

Collins, DJ, TC Hughes, and WM Johnson. "Regiospecific Syntheses of the Monomethylated 3-Phenyldihydro-1,2,4-triazin-6(1H)-ones." Australian Journal of Chemistry 49, no. 4 (1996): 463. http://dx.doi.org/10.1071/ch9960463.

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Unambiguous syntheses of four unreported monomethylated derivatives of 3-phenyldihydro-1,2,4-triazin-6(1H)-ones, namely, the 1-methyl (2), 2-methyl (3), 4-methyl (4) and the imidic O-methyl derivative (5), are described. Regioselectivity was achieved for the synthesis of (2) by addition of ethyl glycinate to the 1,3-dipolar nitrile imine derived from N- methylbenzohydrazonoyl bromide hydrobromide (8). The key step for the synthesis of (3) was addition of benzyl 3-methylcarbazate (14) to ethyl N-[ chloro (phenyl) methylene ] glycinate (15b). The 4-methyl compound (4) was prepared by cycloaddition of ethyl N-( thiobenzoyl ) sarcosinate (21) with hydrazine hydrate, and the O-methyl compound (5) was prepared by reaction of sodium methoxide with 6-chloro-3-phenyl-4,5-dihydro-1,2,4-triazine (23).

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46

Schulze, B�rbel, Dagmar Selke, Sabine Kirrbach, and Rhett Kempe. "Synthese neuer N-Aroylisothiazol-2-imine und N-Aroylamino-isothiazoliumsalze durch Cyclisierung von thiocyanato-substituierten Hydrazonen." Journal f�r Praktische Chemie/Chemiker-Zeitung 336, no. 2 (1994): 115–20. http://dx.doi.org/10.1002/prac.19943360204.

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47

Cordero-Vargas, Alejandro, and Jeferson B. Mateus-Ruiz. "Visible-Light-Mediated Photoredox Reactions in the Total Synthesis of Natural Products." Synthesis 52, no. 21 (2020): 3111–28. http://dx.doi.org/10.1055/s-0040-1707225.

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In the last two decades, the field of photoredox catalysis (PRC) has grown impressively with reports of new synthetic methodologies and more efficient versions of known free-radical reactions. The impressive success of visible-light-mediated photoredox catalysis is, in great part, due to its low environmental impact, mild reaction conditions, clean reactions, and inexpensive methodologies. These features have allowed photoredox catalysis to emerge as a powerful tool in the synthesis of natural products; much excellent work was reported between 2011 and 2015. Since 2016, a number of more efficient and impressive total syntheses of natural products featuring photoredox catalysis have been reported. In this review, we summarize the recent synthetic applications of photoredox catalysis in the total synthesis of natural products between 2016 and 2020.1 Introduction2 Intermolecular Additions from Functionalized Substrates2.1 Intermolecular Additions from Alkyl Halides2.2 Intermolecular Additions from Alcohols and Carboxylic Acids3 Cyclizations from Functionalized Substrates3.1 Cyclizations of Carbon-Centered Radicals3.2 Cyclizations of Nitrogen-Centered Radicals4 Intramolecular Cyclization from Non-functionalized N–H Bonds4.1 Type I Radical Cascade4.2 Type II Radical Cascade4.3 Type III Radical Cascade5 Functionalization of Imines and Enamines6 Cycloadditions7 Miscellaneous7.1 Dehalogenation and Reductive Decarboxylation7.2 Thiyl Radical Promoted Cascade8 Conclusions and Perspectives

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Dölling, Karin, Kurt Merzweiler, Christoph Wagner, and Horst Weichmann. "Synthese, Struktur und Reaktivität von 3-Triorganostannyl-N-diphenylmethylen-alaninestern / Synthesis, Structure and Reactivity of 3-Triorganostannyl-N-diphenylmethylenealanine Esters." Zeitschrift für Naturforschung B 54, no. 3 (1999): 293–99. http://dx.doi.org/10.1515/znb-1999-0301.

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The deprotonation of N-diphenylmethylene-glycine esters, obtained from glycine ester hydrochlorides and benzophenone imine, and reaction of the resulting carbanions with iodomethyl triorganostannanes gives the 3-triorganostannyl-N-diphenylmethylene-alanine esters Me2RSnCH2CH(N=CPh2)COOR′ (1a - e; R = Me, tBu; R′ = Me, Et, tBu, Bz). These title compounds are transformed into their tin monochlorides MeR(Cl)SnCH2CH(N=CPh2)COOR′ (2a - e) by a redistribution reaction with Me2SnCl2. IR and NMR data and the crystal structure of Me2(Cl)SnCH2CH(N=CPh2)COOEt (2b) reveal for 2a - e an intramolecular coordination of the ester C = 0 group at the tin atom. Mild two-phase hydrolysis of 1a - e with 1N HCl gives the 3-triorganostannyl-alanine ester hydrochlorides Me2RSnCH2CH(NH2)COOR′ · HCl (3a - e). The transformation of 3a - e into the corresponding alanine esters Me2RSnCH2CH(NH2)COOR′ (4a - e) could be realized with NH3 in chloroform. 4a - e are of limited thermal stability.

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Ueda, Shigeo, Hideo Terauchi, Akihiro Yano, Motoharu Ido, Masashi Matsumoto, and Motoji Kawasaki. "4,5-Disubstituted-1,3-oxazolidin-2-imine derivatives: a new class of orally bioavailable nitric oxide synthase inhibitor." Bioorganic & Medicinal Chemistry Letters 14, no. 2 (2004): 313–16. http://dx.doi.org/10.1016/j.bmcl.2003.11.010.

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50

YU, DOU, and WILLIAM D. ELDRED. "GABAAand GABACreceptor antagonists increase retinal cyclic GMP levels through nitric oxide synthase." Visual Neuroscience 20, no. 6 (2003): 627–37. http://dx.doi.org/10.1017/s0952523803206052.

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The nitric oxide (NO)/cyclic guanosine monophosphate (cGMP) signal transduction pathway plays a role in every retinal cell type. Previous studies have shown that excitatory glutamatergic synaptic pathways can increase cGMP-like immunoreactivity (cGMP-LI) in retina through stimulation of NO production, but little is known about the role of synaptic inhibition in the modulation of cGMP-LI. Gamma-amino-n-butyric acid (GABA) plays critical roles in modulating excitatory synaptic pathways in the retina. Therefore, we used GABA receptor antagonists to explore the role of GABAergic inhibitory synaptic pathways on the modulation of the NO/cGMP signal-transduction system. Cyclic GMP immunocytochemistry was used to investigate the effects of the GABA receptor antagonists bicuculline, picrotoxin, and (1,2,5,6-tetrahyropyridin-4-yl) methylphosphinic acid (TPMPA) on levels of cGMP-LI. Cyclic GMP-LI was strongly increased in response to the GABAAreceptor antagonist bicuculline, while the GABACreceptor antagonist TPMPA had little effect on cGMP-LI. The GABAA/GABACreceptor antagonist, picrotoxin, caused a moderate increase in cGMP-LI, which was mimicked by the combination of bicuculline and TPMPA. The nitric oxide synthase inhibitor, S-methyl-L-thiocitrulline (SMTC), blocked the increased cGMP-LI in response to stimulation with either bicuculline or picrotoxin. Treatments with either of the glutamate receptor antagonists (5R,10S)-(+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (MK-801) or 6-cyano-7-nitroquinoxaline-2,3-dione (CNQX) partially blocked the increases in cGMP-LI seen in response to bicuculline, but a combination of MK-801 and CNQX completely eliminated these increases. These results suggest that inhibitory synaptic pathways involving both types of GABA receptors work through excitatory glutamatergic receptors to regulate the NO/cGMP signal-transduction pathway in retina.

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