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Synthesis of 2-(5-arylidene-4-oxo-3-arylthiazolydine-2)-N-phenylethanthiamides derivatives from malondithioamides

K. L. Obydennov, N. A. Golovko, Yu. Yu. Morzherin

Abstract


It is shown that thioacetamide are comfortable synthetic blocks for various heterocycles, including thiazole containing a double exocyclic bonds. This work describes the synthesis of (Z)-2-((Z)-5-arylidene-4-oxo-3-arylthiazolidin-2-ylidene)-N-arylethanethioamide 4 obtained from the Knoevenagel condensation of (Z)-2-(4-oxo-3-arylthiazolidin-2-ylidene)-N-arylylethanethioamide 2. The starting material 2 was synthesized by a Hantzsch reaction of N,N`-diarylmalondithioamides 1 and ethyl 2-chloroacetate. The structures of the obtained products were established by NMR and the structural features are discussed. Several 4-oxothiazolidin-2-ylidenes were studied by UV-visible spectroscopy technique

Keywords


thiomalonamides; chromophores; Oxidation reaction; knoevenagel condensation; thiazole

References


Varanasi PR, Jen AK-Y, Chandrasekhar J, Namboothiri INN, Rathna A. The important role of heteroaromatics in the design of efficient second-order nonlinear optical molecules: Theoretical investigation on push-pull heteroaromatic stilbenes. J Am Chem Soc. 1996;118(49):12443-8. doi:10.1021/ja960136q

Ellinger S, Graham KR, Shi P, Farley RT, Steckler TT, Brookins RN,Taranekar P, Mei, J, Padilha LA, Ensley TR, Hu H, Webster S, Hagan DJ, Van Stryland EW, Schanze KS, Reynolds JR. Donor-acceptor-donor-based π-conjugated oligomers for nonlinear optics and near-IR emission. Chem Mater. 2011;23(17):3805-17. doi:10.1021/cm201424a

Andersson AS, Diederich F, Nielsen MB. Acetylenic Tetrathiafulvalene-dicyanovinyl donor-acceptor chromophores. Org Biomol Chem. 2009;7(17):3474-80. doi:10.1039/b909886k

Kivala M, Diederich F. Acetylene-derived strong organic acceptors for planar and nonplanar push-pull chromophores. Acc Chem Res. 2009;42(2):235-48. doi:10.1021/ar8001238

Mahuteau-Betzer F, Piguel S. Synthesis and evaluation of photophysical properties of Series of π-conjugated oxazole dyes. Tetrahedron Lett. 2013;54(24):3188-93. doi:10.1016/j.tetlet.2013.04.037

Facchetti A, Abbotto A, Beverina L, van der Boom ME, Dutta P, Evmenenko G, Marks TJ, Pagani GA. Azinium-(π-bridge)-pyrrole NLO-phores: Influence of heterocycle acceptors on chromophoric and self-assembled thin-film properties. Chem Mater. 2002;14(12):4996-5005. doi:10.1021/cm0205635

Insuasty A, Ortiz A, Tigreros A, Solarte E, Insuasty B, Martín N. 2-(1,1-dicyanomethylene)rhodanine: A novel, efficient electron acceptor. Dyes Pigm. 2011;88(3):385-90. doi:10.1016/j.dyepig.2010.08.11

Baranac-Stojanović M, Kleinpeter E. Quantification of the aromaticity of 2-alkylidenethiazolines subjected to push-pull activity. J Org Chem. 2011;76(10):3861-71. doi:10.1021/jo200294f

Baranac-Stojanović M, Klaumünzer U, Marković R, Kleinpeter E. Structure, configuration, conformation and quantification of the push-pull effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives. Tetrahedron. 2010;66(46):8958-67. doi:10.1016/j.tet.2010.09.040

Insuasty B, Insuasty A, Tigreros A, Quiroga J, Abonia R, Nogueras M, Cobo J, Derita M, Zacchino S. Synthesis and antifungal evaluation of novel dicyanoderivatives of rhodanine. J Heterocycl Chem. 2011;48(2):347-50. doi:10.1002/jhet.565

Galán E, Andreu R, Garín J, Mosteo L, Orduna J, Villacampa B, Diosdado BE. Influence of thiazole regioisomerism on second-order nonlinear optical chromophores. Tetrahedron. 2012;68(32):6427-34. doi:10.1016/j.tet.2012.05.123

Danilkina NA, Mikhailov LE, Ivin BA. Condensations of thioamides with acetylenecarboxylic acid derivatives. Russ J Org Chem. 2006;42(6):783-811. doi:10.1034/S1070428006060017

Britsun VN, Esipenko AN, Lozinskii MO. Heterocyclization of thioamides containing an active methylene group. Chem Heterocycl Compd. 2008;44(12):1429-59. doi:10.1007/s10593-009-0214-x

Dyachenko VD, Chernega AN, Dyachenko SV. Transamination of cyanothioacetamide with morpholine. molecular and crystal structure of 3-(morpholin-1-yl)-3-thioxopropanenitrile and 3-(morpholin-1-yl)- 3-thioxopropanethioamide. Russ J Gen Chem. 2012;82(4):720-4. doi:10.1134/s1070363212040184




DOI: http://dx.doi.org/10.15826/chimtech.2014.1.2.715

Copyright (c) 2014 K. L. Obydennov, N. A. Golovko, Yu. Yu. Morzherin

© Chimica Techno Acta, 2014-2018
ISSN 2411-1414 (Online), ISSN 2409-5613 (Print)

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