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Journal articles on the topic 'Azomethine imine'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 February 2022

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1

Svete, Jurij, Uroš Grošelj, Franc Požgan, and Bogdan Štefane. "Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)." Synthesis 50, no. 23 (October 5, 2018): 4501–24. http://dx.doi.org/10.1055/s-0037-1610284.

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Although the first example of copper-catalyzed azomethine imine–alkyne cycloaddition (CuAIAC) was published only a year after the seminal papers of Meldal and Sharpless on Cu-catalyzed azide–alkyne cycloaddition (CuAAC), the CuAIAC reaction has remained overlooked by the synthetic community for almost a decade. Since 2010, however, CuAIAC reaction started to emerge as a promising supplement to the well-known CuAAC reaction. The present review surveys primarily the literature on CuAIAC reaction since 2003. Beside this, azomethine imine–alkyne cycloadditions catalyzed by other metals, selected examples of metal-free reactions, and related [3+3] and [3+4] cycloadditions of azomethine imines are presented. All these experimental data indicate the viability of CuAIAC in organic synthesis and the applicability in ‘click’ chemistry.1 Introduction2 Reactions with Acyclic Azomethine Imines3 Reactions with C,N-Cyclic Azomethine Imines4 Reactions with N,N-Cyclic Azomethine Imines5 Reactions with C,N,N-Cyclic Azomethine Imines6 The Mechanism of the CuAIAC Reaction7 Conclusions and Outlook

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2

Sikervar, Vikas, Ravindra Sonawane, Raghuramaiah Mandadapu, Amol Satish Dehade, Shrikant Abhiman Shete, and Mark Montgomery. "Lewis Acid Mediated [3+2] and [3+3] Annulations of an Azomethine Imine with Donor–Acceptor Cyclopropanes." Synthesis 53, no. 16 (May 10, 2021): 2865–73. http://dx.doi.org/10.1055/a-1503-8068.

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AbstractTwo different Lewis acids were used for developing [3+2] and [3+3] regioselective cycloaddition reactions of an azomethine imine with activated cyclopropanes. Scandium(III) triflate catalyzes a [3+2] cycloaddition reaction of the azomethine imine with cyclopropanes to form tetrahydropyrazolone derivatives and tricyclic tetrahydrofuran derivatives in moderate yields. Complementary to this, a novel [3+3] cycloaddition reaction of the azomethine imine with activated cyclopropanes was developed by using EtAlCl2 as a Lewis acid to form hexahydropyridazinone derivatives in high regioselectivity.

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3

Kashinath, Dhurke, Kota Sathish, and Sakkani Nagaraju. "Synthesis of Spiro Pyrazolone-Oxindole and Bicyclic Pyrazolone Derivatives via Solvent-Dependent Regioselective Aza-1,4/1,6-Michael and Intramolecular Cycloaddition under Catalyst-Free Conditions." SynOpen 05, no. 02 (April 13, 2021): 123–33. http://dx.doi.org/10.1055/a-1480-9837.

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AbstractA solvent-dependent, highly regioselective [3+2]-cycloaddition reaction of isoxazole-styrenes and azomethine imines under catalyst-free conditions is reported, furnishing a library of pyrazolone–spirooxindole hybrids. Good regioselectivity for the isomeric structures was achieved by the reaction of isoxazole-styrene and azomethine imine in different solvents and temperatures. The developed method was extended for the synthesis of tri-substituted dinitrogen-fused pyrazolones by using a 1,6-Michael addition reaction. Furthermore, the isoxazole moiety was converted into a carboxylic acid as a model study via ring opening.

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4

Li, Yan, and Zhiqiang Zhang. "Mechanisms of phosphine-catalyzed [3+3] cycloaddition of ynones and azomethine imines: a DFT study." New Journal of Chemistry 43, no. 34 (2019): 13600–13607. http://dx.doi.org/10.1039/c9nj01943j.

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5

Zhang, Xueyun, Zisong Qi, Jian Gao, and Xingwei Li. "Rhodium(iii)-catalyzed C–H alkynylation of azomethine ylides under mild conditions." Org. Biomol. Chem. 12, no. 46 (2014): 9329–32. http://dx.doi.org/10.1039/c4ob01596g.

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6

Hu, Shihe, Jian Zhang, and Qiaomei Jin. "DMAP-catalyzed alkylation of isatin N,N′-cyclic azomethine imine 1,3-dipoles with Morita–Baylis–Hillman carbonates." New Journal of Chemistry 42, no. 9 (2018): 7025–29. http://dx.doi.org/10.1039/c8nj00234g.

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7

Ansari, Arshad J., Aabid Abdullah Wani, Antim K. Maurya, Sarika Verma, Vijai K. Agnihotri, Ashoke Sharon, Prasad V. Bharatam, and Devesh M. Sawant. "An unprecedented N- to C-sulfonyl migration in the reaction of azomethine amine and allenoates: access to arylsulfonylmethyl substituted pyrazolo[1,5-c]quinazoline and mechanistic studies." Chemical Communications 55, no. 98 (2019): 14825–28. http://dx.doi.org/10.1039/c9cc06751e.

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8

Suga, Hiroyuki, Masahiro Yoshiwara, Takaaki Yamaguchi, Takashi Bando, Mizuki Taguchi, Ayano Inaba, Yuichi Goto, Ayaka Kikuchi, Kennosuke Itoh, and Yasunori Toda. "Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system." Chemical Communications 55, no. 11 (2019): 1552–55. http://dx.doi.org/10.1039/c8cc09224a.

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9

Inturi, Surendra Babu, Biswajit Kalita, and A. Jafar Ahamed. "I2-TBHP-catalyzed one-pot highly efficient synthesis of 4,3-fused 1,2,4-triazoles from N-tosylhydrazones and aromatic N-heterocycles via intermolecular formal 1,3-dipolar cycloaddition." Organic & Biomolecular Chemistry 14, no. 47 (2016): 11061–64. http://dx.doi.org/10.1039/c6ob01926a.

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10

Liu, Anan, Dongge Ma, Yuhang Qian, Jundan Li, Shan Zhai, Yi Wang, and Chuncheng Chen. "A powerful azomethine ylide route mediated by TiO2 photocatalysis for the preparation of polysubstituted imidazolidines." Organic & Biomolecular Chemistry 19, no. 10 (2021): 2192–97. http://dx.doi.org/10.1039/d0ob02277b.

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11

Moghaddam, F. Matloubi, M. Eslami, A. Siahpoosh, and G. Hoda. "Diastereoselective construction of a functionalized dihydro-pyridazine-based spirooxindole scaffold via C-3 umpolung of isatin N,N′-cyclic azomethine imine." New Journal of Chemistry 43, no. 26 (2019): 10318–23. http://dx.doi.org/10.1039/c8nj06345a.

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This study demonstrates an abnormal [3+3] tandem Michael addition/N-cyclization of isatin N,N′-cyclic azomethine imine 1,3-dipoles and 2-arylidene malononitrile that diastereoselectively construct a dihydro-pyridazine-based spirooxindole.

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12

Hamidian, Kourosh, Mohsen Irandoust, Ezzat Rafiee, and Mohammad Joshaghani. "Synthesis, Characterization, and Tautomeric Properties of Some Azo-azomethine Compounds." Zeitschrift für Naturforschung B 67, no. 2 (February 1, 2012): 159–64. http://dx.doi.org/10.1515/znb-2012-0208.

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The primary azo compound 1-(3-formyl-4-hydroxyphenylazo)-4-nitrobenzene reacts with some aliphatic and aromatic diamines and yields the corresponding azo-azomethine compounds. These compounds were characterized by elemental analysis, IR, UV/Vis, and NMR spectroscopy. The primary azo compound exists entirely in the azo form in solution as well as in the solid phase. The tautomeric structure of azo-azomethine compounds heavily depends on the solvent and the substituents. Aliphatic diamine-based compounds favor the enol-imine tautomer while aromatic diamine-based compounds have structures that lie between the two enol-imine and keto-amine tautomers due to a relatively strong intramolecular hydrogen bond. The compounds exhibit positive solvatochromism (bathochromic shift) so that their absorption bands move toward longer wavelengths as the polarity of the solvents increases. In addition, UV/Vis spectrophotometry has shown that the studied compounds have molar extinction coefficients larger than 40000.

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13

Fishwick, Colin W. G., Ronald Grigg, Visuvanathar Sridharan, and Julia Virica. "Sequential azomethine imine cycloaddition–palladium catalysed cyclisation processes." Tetrahedron 59, no. 24 (June 2003): 4451–68. http://dx.doi.org/10.1016/s0040-4020(03)00517-9.

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14

Monnier, Karin, Gérard Schmitt, Bernard Laude, Marie-France Mercier, Marek M. Kubicki, and Michel Jannin. "Étude de la stéréochimie de la réaction de cycloaddition dipolaire-1,3 de quelques 5-phényl-3,6-dihydro-2H-1,4-oxazin-2-ones avec les N-méthyl et N-phénylmaléimides." Canadian Journal of Chemistry 73, no. 2 (February 1, 1995): 181–90. http://dx.doi.org/10.1139/v95-027.

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Six derivatives of 5-phenyl-3,4-dihydro-2H-1,4-oxazin-2-ones 1 were synthetized from α-amino acids. These compounds are precursors of six-membered cyclic azomethine ylids involving one stereocenter. The 1,3-dipolar species react with N-methyl and N-phenylmaleimides, leading diastereospecifically to cycloadducts where the approach of the dipolarophile occurs from the less hindered side of the 1,3-dipole and with the maleimido moiety in an exo position. Unfortunately, racemization was observed during the cycloaddition reaction, presumably owing to reversible imine–enamine transformation. Keywords: α-amino acids, cyclic azomethine ylids, diastereospecificity.

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15

Choi, Anthony, Jemma Castle, Rungroj Saruengkhanphasit, and Iain Coldham. "Synthesis of Spirocyclic Amines by 1,3-Dipolar Cycloaddition of Azomethine Ylides and Azomethine Imines." Synthesis 52, no. 08 (January 27, 2020): 1273–78. http://dx.doi.org/10.1055/s-0039-1691588.

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Simple ketone starting materials with a halide leaving group and an alkene were prepared in one step and heated with glycine or glycine esters to promote a tandem imine formation, cyclization, and dipolar cycloaddition cascade. The chemistry was also feasible with acetylhydrazide. In each case a single stereoisomer of the tricyclic amine or pyrazolidine product was formed and the stereochemistry was verified by single crystal X-ray diffraction. When the reaction with glycine, which occurs with loss of CO2, was unsuccessful, the cascade process could be promoted by cross metathesis to give the vinyl sulfone starting material that provides a more reactive dipolarophile. Reductive cleavage of the pyrazolidine gave a spirocyclic diamine product.

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16

Marin, Luminita, Arie van der Lee, Sergiu Shova, Adina Arvinte, and Mihail Barboiu. "Molecular amorphous glasses toward large azomethine crystals with aggregation-induced emission." New Journal of Chemistry 39, no. 8 (2015): 6404–20. http://dx.doi.org/10.1039/c5nj01052g.

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Imine compounds containing rigid cores and soft aliphatic tails have been designed to generate molecular glasses and large crystals displaying aggregation-induced emission, which makes them interesting candidates for optoelectronic applications.

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17

Molchanov, Alexander P., Mariia M. Efremova, Mariya A. Kryukova, and Mikhail A. Kuznetsov. "Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation." Beilstein Journal of Organic Chemistry 16 (October 30, 2020): 2679–86. http://dx.doi.org/10.3762/bjoc.16.218.

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The first example of the cycloaddition of in situ-generated azomethine imine under microwave conditions is described. The reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones proceeds regio- and stereoselectively giving mostly good yields of the corresponding perhydropyrazolopyrazoles. The products of the reaction undergo cycloreversion under the reaction conditions.

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18

Ramachary, Dhevalapally B., T. Prabhakar Reddy, and A. Suresh Kumar. "Organocatalytic azomethine imine-olefin click reaction: high-yielding stereoselective synthesis of spiroindane-1,3-dione-pyrazolidinones." Organic & Biomolecular Chemistry 14, no. 27 (2016): 6517–22. http://dx.doi.org/10.1039/c6ob01009a.

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We present herein a new click reaction for the synthesis of drug-like spiroindane-1,3-dione-pyrazolidinones from indane-1,3-diones, aldehydes and N,N-cyclic azomethine imines through amino acid-catalysis.

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19

Yue, Guizhou, Zhengjie Dou, Zexi Zhou, Li Zhang, Juhua Feng, Huabao Chen, Zhongqiong Yin, et al. "Rapid abnormal [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones." New Journal of Chemistry 44, no. 21 (2020): 8813–17. http://dx.doi.org/10.1039/d0nj00887g.

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More than 35 new compounds were prepared rapidly in moderate to excellent yields with high diastereoselectivities by K₂CO₃-promoted abnormal 1,3-diploar cycloaddition of isatin N, N′-cyclic azomethine imines with chalcones.

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20

Kassim, Muhammad Arif, Ubaidullah H. M. Yassin, Ai Ling Tan, Anwar Usman, and Malai Haniti S. A. Hamid. "[1-(Pyrazin-2-yl)ethylidene]hydrazine: a new multitopic ligand for the design of hybrid molecular frameworks." Acta Crystallographica Section C Structural Chemistry 74, no. 4 (March 7, 2018): 424–27. http://dx.doi.org/10.1107/s2053229618003273.

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Hydrazones and their derivatives are closely related to imine compounds and are potential antimicrobial agents. They have also found application in supramolecular chemistry as multitopic ligands to link multiple metal centres for the design of hybrid molecular frameworks. The molecule of the title compound, C6H8N4, consists of an imine linkage with an N—N bond length of 1.3540 (14) Å. This asymmetric compound is nearly planar and adopts an E configuration about the azomethine C=N double bond. In the solid state, there are two intermolecular N—H...N interactions that interconnect the molecules into a two-dimensional network. The three-dimensional arrangement of the crystal packing is further stabilized by intermolecular π–π interactions interconnecting the centroids of the heterocyclic rings.

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21

Sreeja, P. B., M. Sithambaresan, N. Aiswarya, and M. R. Prathapachandra Kurup. "N′-[(1E)-1-(2-Fluorophenyl)ethylidene]pyridine-3-carbohydrazide." Acta Crystallographica Section E Structure Reports Online 70, no. 2 (January 8, 2014): o115. http://dx.doi.org/10.1107/s1600536813035009.

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The title compound, C14H12FN3O, adopts anEconformation with respect to the azomethine double bond whereas the N and methyl C atoms are in aZconformation with respect to the same bond. The ketonic O and azomethine N atoms arecisto each other. The non-planar molecule [the dihedral angle between the benzene rings is 7.44 (11)°] exists in an amido form with a C=O bond length of 1.221 (2) Å. In the crystal, a bifurcated N—H...(O,N) hydrogen bond is formed between the amide H atom and the keto O and imine N atoms of an adjacent molecule, leading to the formation of chains propagating along theb-axis direction. Through a 180° rotation of the fluorophenyl ring, the F atom is disordered over two sites with an occupancy ratio of 0.632 (4):0.368 (4).

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22

Roussi, Fanny, Martine Bonin, Angèle Chiaroni, Laurent Micouin, Claude Riche, and Henri-Philippe Husson. "Asymmetric 1,3-dipolar cycloadditions of a chiral non-racemic azomethine imine." Tetrahedron Letters 40, no. 19 (May 1999): 3727–30. http://dx.doi.org/10.1016/s0040-4039(99)00610-3.

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23

Chung, Florence, Ariane Chauveau, Mohamed Seltki, Martine Bonin, and Laurent Micouin. "Asymmetric 1,3-dipolar cycloadditions of a chiral nonracemic glyoxylic azomethine imine." Tetrahedron Letters 45, no. 15 (April 2004): 3127–30. http://dx.doi.org/10.1016/j.tetlet.2004.02.088.

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24

Sau, Madan, Kshitiz Verma, and Tapas Das. "Synthesis of N‐heterocycles via [4 + 3] cycloaddition of azomethine imine." Journal of Heterocyclic Chemistry 57, no. 11 (August 27, 2020): 3722–34. http://dx.doi.org/10.1002/jhet.4095.

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25

Zhang, Min, Feifei Wu, Huanhong Wang, Junshi Wu, and Wanzhi Chen. "Copper-Catalyzed Sequential Azomethine Imine-Alkyne Cycloaddition and Umpolung Thiolation Reactions." Advanced Synthesis & Catalysis 359, no. 16 (June 19, 2017): 2768–72. http://dx.doi.org/10.1002/adsc.201700387.

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26

Temizkan, Kevser, and İsmet Kaya. "Heat resisting and water-soluble chocolate polyesters containing azomethine group." Materials Science-Poland 35, no. 2 (July 26, 2017): 303–12. http://dx.doi.org/10.1515/msp-2017-0018.

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Abstract In this study, soluble in water poly(azomethine-ester)s (PAEs) were synthesized via elimination reactions of aromatic dihydroxy compounds containing imine bonding with terephthaloyl chloride. The structures of Schiff bases (SBs) and PAEs containing different aliphatic chains were confirmed by FT-IR, 1H-NMR, 13C-NMR and UV-Vis analyses. Physicochemical properties of the new polymers were characterized. Thermal properties of the compounds were investigated by TGA-DTA, DMA and DSC. According to TGA measurements, the starting degradation temperatures (Ton) of P-1, P-2, P-3, and P-4 poly(azomethine-ester)s were found as 255 °C, 232 °C, 222 °C, and 221 °C, respectively. The starting degradation temperatures of the poly(azomethine-ester)s were higher than their Schiff base compounds. According to dynamical mechanical analysis (DMA) measurements, glass transition temperature (Tg) of P-1, P-2, P-3, and P-4 poly(azomethine-ester)s were found as 95 °C, 138 °C, 140 °C, and 145 °C, respectively. The morphological and topographic properties of the PAEs containing azomethine linkage in the main chain were investigated by FE-SEM and AFM, respectively. The molecular mass distributions of PAEs were determined by gel permeation chromatography (GPC). Electrochemical (E′g) and optical band gap (Eoptg ) values of the prepared SBs and PAEs were calculated from cyclic voltammetry (CV) and UV-Vis analyses. The electrochemical band gap (E′g) values of P-1, P-2, P-3 and P-4 were found as 2.44 eV, 2.41 eV, 2.39 eV and 2.39 eV, respectively, from the cyclic voltammetry.

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27

Schwan, Adrian L., and John Warkentin. "The synthesis and unimolecular decomposition of four novel Δ1-1,2,4-triazolines." Canadian Journal of Chemistry 66, no. 9 (September 1, 1988): 2285–93. http://dx.doi.org/10.1139/v88-362.

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Treatment of 4-tert-butyl-3,3-dimethyl-5-methylene-Δ1-1,2,4-triazoline (3) with benzonitrile oxide (9), diphenylnitrile imine (10), phenyl azide, and p-nitrophenyl azide led, in each case, to 1,3-dipolar cycloaddition. The products, Δ1-1,2,4-tri-azolines that are spiro-fused to another 5-membered ring, could be isolated in pure form in three of the four cases. All four are thermally unstable and decompose by loss of N2 from the Δ1-1,2,4-triazoline moiety to form an azomethine ylide. Subsequent reactions of those ylides are described.

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28

Xie, Haibo, Jiangtao Zhu, Zixian Chen, Shan Li, and Yongming Wu. "Diastereoselective Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with Fluorinated Imine." Journal of Organic Chemistry 75, no. 21 (November 5, 2010): 7468–71. http://dx.doi.org/10.1021/jo101447n.

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29

Li, Bao-Sheng, Yuhuang Wang, Zhichao Jin, and Yonggui Robin Chi. "Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts." Chemical Science 6, no. 10 (2015): 6008–12. http://dx.doi.org/10.1039/c5sc01972a.

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30

Ansari, Arshad J., Ramdas S. Pathare, Anita Kumawat, Antim K. Maurya, Sarika Verma, Vijai K. Agnihotri, Rahul Joshi, et al. "A diversity-oriented synthesis of polyheterocycles via the cyclocondensation of azomethine imine." New Journal of Chemistry 43, no. 35 (2019): 13721–24. http://dx.doi.org/10.1039/c9nj02874a.

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31

Maiti, Dilip K., Nirbhik Chatterjee, Palash Pandit, and Sandip K. Hota. "Generation of azomethine imine and metal-free formal 1,3-dipolar cycloaddition of imine with PhIO: reaction, scope, and synthesis." Chemical Communications 46, no. 12 (2010): 2022. http://dx.doi.org/10.1039/b924761k.

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32

Wang, Zhan-Yong, Ting Yang, Rongxiang Chen, Xueji Ma, Huan Liu, and Kai-Kai Wang. "1,3-Dipolar cycloaddition of isatin N,N′-cyclic azomethine imines with α,β-unsaturated aldehydes catalyzed by DBU in water." RSC Advances 10, no. 41 (2020): 24288–92. http://dx.doi.org/10.1039/d0ra03806g.

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A simple and green procedure was established by [3 + 3] cycloaddition reaction of isatin derived cyclic imine 1,3-dipoles with α,β-unsaturated aldehydes, giving spirooxindoles with aza-quaternary center in good yields and diastereoselectivities.

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33

Pušavec Kirar, Eva, Uroš Grošelj, Giorgio Mirri, Franc Požgan, Gregor Strle, Bogdan Štefane, Vasko Jovanovski, and Jurij Svete. "“Click” Chemistry: Application of Copper Metal in Cu-Catalyzed Azomethine Imine–Alkyne Cycloadditions." Journal of Organic Chemistry 81, no. 14 (July 2016): 5988–97. http://dx.doi.org/10.1021/acs.joc.6b00945.

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34

Das, Tapas, Madan Sau, Bishnu Daripa, Dipanjan Karmakar, and Sayan Chakraborty. "[3+3] Cycloaddition of Azomethine Imine: Synthesis of Bi‐ or Tricyclic N‐Heterocycle." ChemistrySelect 5, no. 25 (July 3, 2020): 7605–26. http://dx.doi.org/10.1002/slct.202001674.

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35

Li, Zhao, Naoya Kumagai, and Masakatsu Shibasaki. "Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α,β-Unsaturated Amide and Azomethine Imine." Chemical and Pharmaceutical Bulletin 68, no. 6 (June 1, 2020): 552–54. http://dx.doi.org/10.1248/cpb.c20-00130.

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36

Kajal, Anu, Suman Bala, Sunil Kamboj, Neha Sharma, and Vipin Saini. "Schiff Bases: A Versatile Pharmacophore." Journal of Catalysts 2013 (August 27, 2013): 1–14. http://dx.doi.org/10.1155/2013/893512.

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Schiff bases are condensation products of primary amines with carbonyl compounds gaining importance day by day in present scenario. Schiff bases are the compounds carrying imine or azomethine (–C=N–) functional group and are found to be a versatile pharmacophore for design and development of various bioactive lead compounds. Schiff bases exhibit useful biological activities such anti-inflammatory, analgesic, antimicrobial, anticonvulsant, antitubercular, anticancer, antioxidant, anthelmintic, antiglycation, and antidepressant activities. Schiff bases are also used as catalysts, pigments and dyes, intermediates in organic synthesis, polymer stabilizers, and corrosion inhibitors. The present review summarizes information on the diverse biological activities and also highlights the recently synthesized numerous Schiff bases as potential bioactive core.

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37

Agbese, S. A., G. A. Shallangwa, and S. O. Idris. "Synthesis, Characterization and Antimicrobial Evaluation of Mn(II) and Zn(II) Schiff base Complexes with p-hydroxypropiophenone moiety." NIGERIAN ANNALS OF PURE AND APPLIED SCIENCES 1 (March 14, 2019): 202–8. http://dx.doi.org/10.46912/napas.46.

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The Schiff base was synthesized by condensing 4-aminopyridine with 4-hydroxypropiophenone. The synthesized ligand was characterized by proton and carbon-13 NMR spectroscopy, electronic spectroscopy and FTIR.The result of the FTIR showed the presence of a band at 1643.41cm-1 assigned to the azomethine bond, also the result of the 1HNMR and 13CNMR gave credence to the successful synthesis of the Schiff base. The Mn(II) and Zn(II) complexes were characterized by UV-visible analysis, FTIR, molar conductivity measurement and magnetic susceptibility test. The results of the FTIR suggest that the metal complexes possess coordinated water molecules and the shift in the wavenumber of the azomethine linkage in the spectra of the complexes shows that the nitrogen of the imine bond participated in the coordination to the metal centre. The magnetic susceptibility measurement shows that the metal complexes possess octahedral geometry. The molar conductivity test shows that the complexes are nonelectrolytic in nature and the metal to ligand ratio is 1:2. The synthesized ligand and the metal complexes were evaluated for biological activities against some organisms. The Zn(II) complex showed significant activity against the test organisms.

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38

Maiti, Dilip K., Nirbhik Chatterjee, Palash Pandit, and Sandip K. Hota. "ChemInform Abstract: Generation of Azomethine Imine and Metal-Free Formal 1,3-Dipolar Cycloaddition of Imine with PhIO: Reaction, Scope, and Synthesis." ChemInform 41, no. 30 (July 1, 2010): no. http://dx.doi.org/10.1002/chin.201030138.

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39

Coldham, Iain, Adam J. M. Burrell, Hélène D. S. Guerrand, Luke Watson, Nathaniel G. Martin, and Niall Oram. "Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy." Beilstein Journal of Organic Chemistry 8 (January 18, 2012): 107–11. http://dx.doi.org/10.3762/bjoc.8.11.

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Heating aldehydes that contain a protected hydroxymethyl group, a tethered alkyl chloride and a tethered alkenyl group at the α-position of the aldehyde with an amine sets up a cascade (tandem) reaction sequence involving condensation to an intermediate imine, then cyclization and formation of an intermediate azomethine ylide and then intramolecular dipolar cycloaddition. The fused tricyclic products are formed with complete or very high stereochemical control. The hydroxymethyl group was converted into an aldehyde – which could be removed to give the tricyclic amine products that are unsubstituted at the ring junction positions – or was converted into an alkene, which allowed the formation of the core ring system of the alkaloids scandine and meloscine.

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40

Mossine, Valeri V., Steven P. Kelley, and Thomas P. Mawhinney. "Intramolecular 1,5-S...N σ-hole interaction in (E)-N′-(pyridin-4-ylmethylidene)thiophene-2-carbohydrazide." Acta Crystallographica Section E Crystallographic Communications 76, no. 4 (March 17, 2020): 557–61. http://dx.doi.org/10.1107/s2056989020003011.

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The title compound, C11H9N3OS, (I), crystallizes in the monoclinic space group P21/n. The molecular conformation is nearly planar and features an intramolecular chalcogen bond between the thiophene S and the imine N atoms. Within the crystal, the strongest interactions between molecules are the N—H...O hydrogen bonds, which organize them into inversion dimers. The dimers are linked through short C—H...N contacts and are stacked into layers propagating in the (001) plane. The crystal structure features π–π stacking between the pyridine aromatic ring and the azomethine double bond. The calculated energies of pairwise intermolecular interactions within the stacks are considerably larger than those found for the interactions between the layers.

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41

Shunmugaperumal, Selvaraj, Saranya Dhasarathan, Kamatchi P. Selvaraj, Ilango Kaliappan, and Bathula Siva Kumar. "Spectral and Electrochemical Sensing Studies of Unsymmetrical Schiff Bases having Enhanced Antifungal Activity." Asian Journal of Chemistry 33, no. 10 (2021): 2400–2410. http://dx.doi.org/10.14233/ajchem.2021.23351.

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Novel unsymmetrical Schiff bases comprising azomethine spin-off having ferrocene moiety at one end and simple aromatic component attached imine at other end, capable of sensing multiple metal ions have been synthesized. The MLCT charge transfer band in UV-Visible studies upon coordination with metal ions with receptors is recorded particularly for Cu2+ ions. The observed ΔEp values with change in scan rate for metal free and metal added receptor solution suggest quasi-reversible process. Agar well diffusion method and molecular docking studies reveals that the synthesized compounds inhibit more efficiently fungi rather than bacteria, which hampers the progress of microbial research, as the available antifungal agents are minimal compared to antibacterial counterpart.

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42

Arrieta, Ana, José Ramón Carrillo, Fernando P. Cossío, Angel Díaz-Ortiz, María JoséGómez-Escalonilla, Antonio de la Hoz, Fernando Langa, and Andrés Moreno. "Efficient tautomerization hydrazone-azomethine imine under microwave irradiation. Synthesis of [4,3′] and [5,3′]bipyrazoles." Tetrahedron 54, no. 43 (October 1998): 13167–80. http://dx.doi.org/10.1016/s0040-4020(98)00798-4.

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43

Garner, Philip, and H. Ümit Kaniskan. "A stereodivergent cascade imine→azomethine ylide→1,3-dipolar cycloadditive approach to α-chiral pyrrolidines." Tetrahedron Letters 46, no. 31 (August 2005): 5181–85. http://dx.doi.org/10.1016/j.tetlet.2005.05.119.

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44

Xie, Haibo, Jiangtao Zhu, Zixian Chen, Shan Li, and Yongming Wu. "ChemInform Abstract: Diastereoselective Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with Fluorinated Imine." ChemInform 42, no. 8 (January 27, 2011): no. http://dx.doi.org/10.1002/chin.201108127.

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Li, Bao-Sheng, Yuhuang Wang, Zhichao Jin, and Yonggui Robin Chi. "ChemInform Abstract: Cycloaddition of Cyclobutenone and Azomethine Imine Enabled by Chiral Isothiourea Organic Catalysts." ChemInform 47, no. 5 (January 2016): no. http://dx.doi.org/10.1002/chin.201605178.

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46

Fuchi, Nobuhiro, Takayuki Doi, and Takashi Takahashi. "A Library Synthesis of Pyrazoles by Azomethine Imine Cycloaddition to the Polymer-supported Vinylsulfone." Chemistry Letters 34, no. 3 (March 2005): 438–39. http://dx.doi.org/10.1246/cl.2005.438.

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Yu, Bo, Ke-Fang Yang, Xing-Feng Bai, Jian Cao, Zhan-Jiang Zheng, Yu-Ming Cui, Zheng Xu, Li Li, and Li-Wen Xu. "Ligand-Controlled Inversion of Diastereo- and Enantioselectivity in Silver-Catalyzed Azomethine Ylide–Imine Cycloaddition of Glycine Aldimino Esters with Imines." Organic Letters 20, no. 9 (April 17, 2018): 2551–54. http://dx.doi.org/10.1021/acs.orglett.8b00702.

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48

Hajós, György, Zsuzsanna Riedl, Orsolya Egyed, Branko Stanovnik, Csilla Gróf, and Antal Csámpai. "Regio- and Stereoselective Cycloadditions and Further Transformations of Azomethine Imine Derivatives of Fused [1,2,4]Triazines." HETEROCYCLES 65, no. 8 (2005): 1889. http://dx.doi.org/10.3987/com-05-10434.

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Shinde, Anand H., Shinde Vidyacharan, and Duddu S. Sharada. "Microwave-assisted facile synthesis of [a]-annelated pyrazolopyrroloindoles via intramolecular azomethine imine 1,3-dipolar cycloaddition." Tetrahedron Letters 55, no. 19 (May 2014): 3064–69. http://dx.doi.org/10.1016/j.tetlet.2014.03.134.

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Bakthadoss, Manickam, and Vishal Agarwal. "Synthesis of Highly Functionalized Tricyclic Chromenopyrazole Frameworks via Intramolecular Azomethine Imine 1,3-Dipolar Cycloaddition (IAIDC)." ChemistrySelect 3, no. 24 (June 26, 2018): 6960–64. http://dx.doi.org/10.1002/slct.201801269.

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