The Behavior of (cyclic-alkylidene)hydrazinecarbothioamides in Cyclization with Dimethyl acetylenedicarboxylate

Hassan A. A., Mohamed S. K., Mohamed N. K., El-Shaieb K. M. A., Abdel-Aziz A. T., Mague J. T., ...More

JOURNAL OF HETEROCYCLIC CHEMISTRY, vol.54, no.3, pp.2043-2053, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 54 Issue: 3
  • Publication Date: 2017
  • Doi Number: 10.1002/jhet.2803
  • Journal Name: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2043-2053
  • Erciyes University Affiliated: Yes

Abstract

A series of (Z)-methyl 2(Z)-3-substituted-2-(cycloalkylidenehydrazono)-4-oxothiazolidin-5-ylidene)-acetate derivatives were synthesized via condensation alkylidene-N-substituted hydrazinecarbothioamides with dimethyl acetylenedicarboxylate. The synthesized compounds were characterized by using different spectroscopic methods and confirmed by single crystal X-ray analysis. The behavior of (cyclic-alkylidene) hydrazinecarbothioamides in cyclization was presented. The mechanism of transformation of (Z)-methyl 2-((Z)-3-(cyclopentylideneamino)-4-oxo-2-(phenylimino)thiazolidin-5-ylidene)acetate (14) into the more stable (Z)-Methyl 2-[(Z)-2-(cyclopentylidenehydrazono)-4-oxo-3-phenylthiazolidin-5-ylidene]acetate (5a) was discussed and confirmed.