A Convenient Synthesis of Some New Thiazole and Pyrimidine Derivatives Incorporating a Naphthalene Moiety. (February 2013)

• Record Type: Journal Article
• Authors: Gomha, Sobhi M.; Badrey, Mohamed G.
• Is Part Of: Journal of chemical research. Volume 37:Number 2(2013)
• Page Start: 86
• Page End: 90
• Publication Date: 2013-02
• Subjects: thiazoles -- thiosemicarbazide -- hydrazonoyl halides; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751912X13567137687630
• Languages: English
• ISSNs: 1747-5198

Abstract

The reaction of 2-[1-(naphthalen-2-yl)ethylidene]hydrazinecarbothioamide with hydrazonoyl halides afforded new thiazole derivatives, whilst reaction with compounds containing an activated double bond such as ethoxymethylene-malononitrile and benzylidenemalononitrile yielded the respective pyrimidine derivatives. A 4-thiazolidin-4-one was obtained by reaction of the hydrazinecarbothioamide with ethyl bromoacetate. Subsequent condensation of the thia-zolidinone with aromatic aldehydes afforded the corresponding arylidene derivatives. Treatment of the hydrazinecarbothioamide with dimethyl acetylenedicarboxylate resulted in the formation of a (methoxycarbonylmethylidene) thiazolinone. Reaction of the hydrazinecarbothioamide with 2-chloro-1, 3-dicarbonyl compounds gave the respective thiazole derivatives. The structures of the newly synthesised compounds were confirmed by their elemental analysis and spectral data.