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Studies on the reaction of N-(3-carbethoxy-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)-N′-phenylthiourea with hydrazine hydrate (Part 1)

✍ Scribed by Hassan A. H. El-Sherief; Galal M. El-Naggar; Zeinab A. Hozien; Suliman M. El-Sawaisi

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
467 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image

The reaction of N‐(3‐carbethoxy‐4,5,6,7‐tetrahydrobenzo[b]thien‐2‐yl)‐N′‐phenylthiourea (1) with hydrazine hydrate in 1‐butanol afforded a mixture of compounds 2, 3 and 4. Treatment of 3 and 4 with nitrous acid gave 6 and 8 respectively, while reactions of 3 with acetylacetone gave 7. Synthesis of tetracyclic compounds 9a‐f and 11 from the reactions of 3 with ethyl orthoformate or appropriate acids, acid chloride, carbon disulphide and/or ethyl chloroformate. Also its reaction with isothiocyanate derivatives gave the corresponding thiosemicarbzides 12a,b which on, refluxing in alcoholic KOH gave the unexpected tetracyclic products 14a,b. Similarly the tetracyclic compounds 16a‐e and 19 were obtained by cyclization of 4 and 18 respectively.

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