165609-06-3Relevant academic research and scientific papers
DIHETEROARYLMETHANES. II. ACTIVE METHYLENE BEHAVIOUR OF 2-THIAZOLYL AND 2-OXAZOLYL DERIVATIVES
Abbotto, Alessandro,Bradamante, Silvia,Pagani, Giorgio A.
, p. 301 - 308 (2007/10/02)
The methylene group of bis(2-benzothiazolyl)methane (bbtmH), 1, bis(2-benzoxazolyl)methane (bbomH), 2, and bismethane, 3, undergoes azo-coupling with benzenediazonium chloride to the corresponding phenylhydrazono derivatives, nitrosation with nitrous acid to the corresponding oximes, and crotonic-type condensation with alkyl, aryl, and heteroaryl aldehydes.In the condensation of bbomH, 2, with salicylaldehyde, one of the benzoxazole moieties undergoes ring opening and the final product is a coumarin derivative.The methylene group of 1 and 3 is also sensitive to oxidation by air in alkaline solution leading to the corresponding carbonyl compounds 15 and 17.The analogous reaction carried out on bbomH was found to be sluggish.The behaviour of these diheteroarylmethanes thus conforms with the one typically exhibited by "active" methylene compounds, substituted by efficient electron-withdrawing groups.
