The synthesis and cyclofunctionalization of (1,3-thiazolidin-2-ylidene)ketones

Authors

  • M. B. Litvinchuk Lesya Ukrainka East European National University; Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • A. V. Bentya Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • N. Yu. Slyvka Lesya Ukrainka East European National University, Ukraine
  • M. V. Vovk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.18.951

Keywords:

N-allylthioamides, electrophilic cyclization, (1, 3-thiazolidin-2-ylidene)ketones, tautomerism, pyrrolo[2, 1-b][1, 3]thiazoles, [1, 3]thiazolo[3, 2-a]pyridines

Abstract

Aim. To develop a new approach to the design of (1,3-thiazolidin-2-ylidene)ketones and expansion of their synthetic potential as convenient building blocks in the reactions of [3+2]- and [3+3]-cyclization.

Results and discussion. Еlectrophilic intramolecular cyclization (EIC) of N-allythioamides of β-ketoacids using phosphoric acid or iodine is a convenient synthetic method to obtain new (5-methyl- and 5-iodomethyl-1,3-thiazolidine-2-ylidene)ketones. Cyclization of ketones with maleic anhydride leads to derivatives of 2,3-dihydropyrrolo[2,1-b][1,3]thiazole. [3+3]-Cyclocondensation with methyl propiolate and dimethyl acetylenedicarboxylate results in formation of the functionalized [1,3]thiazolo[3,2-a]pyridine derivatives.

Experimental part. (5-Methyl- and 5-iodomethyl-1,3-thiazolidin-2-ylidene)ketones were synthesized from N-allylthioamides using phosphoric acid or iodine in chloroform. (1,3-Thiazolidin-2-ylidene)ketones react with maleic anhydride, methyl acetylenecarboxylate or dimethyl acetylenedicarboxylate resulting in a 2,3-dihydropyrrolo[2,1-b][1,3]thiazole-5(6H)-one and 2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyridine derivatives.

Conclusions. A convenient method of [5-methyl- and 5-iodomethyl-1,3-thiazolidin-2-ylidene]ketones preparation based on the EIC of N-allylthioamides of β-ketoacids has been developed using phosphoric acid and iodine. The (1,3-thiazolidin-2-ylidene)ketones synthesized can be useful in cyclization reactions leading to functional pyrrolo[2,1-b][1,3]thiazole and [1,3]thiazolo[3,2-a]pyridine derivatives.

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2018-12-14

How to Cite

(1)
Litvinchuk, M. B.; Bentya, A. V.; Slyvka, N. Y.; Vovk, M. V. The Synthesis and Cyclofunctionalization of (1,3-Thiazolidin-2-ylidene)ketones. J. Org. Pharm. Chem. 2018, 16, 18-27.

Issue

Vol. 16 No. 4(64) (2018)

Section

Original Researches

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