The Reaction of 2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophenes with Benzoyl-Isothiocyanate: Synthesis of Annulated Thiophene Derivatives and Their Antitumor Evaluations

Karam Ahmed El-Sharkawy, Hend Mohamed El-Sehrawi, Rehab Ali Ibrahim

Department of Organic Chemistry, Faculty of Pharmacy, October University for Modern Sciences and Arts, El-Wahat Road, 6th of October City, Egypt.
Higher Institute of Engineering and Technology, El-Tagammoe El-Khames, New Cairo, Egypt.
Pharmaceutical Chemistry Department, Faculty of Pharmacy (Girls), Al-Azhar University, Nasr City, Cairo, Egypt.

DOI: 10.4236/ijoc.2012.22020                

Abstract

The reaction of the tetrahydrobenzo[b]thiophene derivatives 1a,b with benzoylisothiocyanate (2) afforded the thiourea derivatives 3a,b. Cyclization of the latter products gave the annulated products 4a,b. Compounds 3a,b reacted with either hydrazine hydrate (5a) or phenyl hydrazine (5b) afforded compounds 7a-d which underwent cyclization for compounds 7a,c afforded compound 9. On the other hand compounds 4a,b reacted with either hydrazine hydrate (5a) or phenyl hydrazine (5b) afforded compounds 6a-d a second pathway was applied to synthesize compound 6c which underwent cyclization afforded compound 9. Also compounds 4a,b reacted with either phenacyl bromide (10) afforded compounds 11a,b or ethylchloroacetae (12) compounds 13a,b were produced. The latter products reacted with each hydrazine hydrate (5a) and phenyl hydrazine (5b) afforded compounds 14a-d. Their antitumor activities were tested using three different cell lines.

Keywords

Tetrahydrobenzo[b]thiophene; Pyrimidine; Thiourea; Antitumor Activity

Conflicts of Interest

The authors declare no conflicts of interest.

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