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Reactions of 2-Cyanomethyl-3,1-benzoxazin-4(H)-one: Synthesis of Quinazoline and 4H-3,1-Benzothiazine Derivatives and Other Heterocycles
Essawy, A.,El-Hashash, M. A.,Mohamed, M. M.
, p. 663 - 666 (2007/10/02)
Reactions of 2-cyanomethyl-3,1-benzoxazin-4(H)-one (1a) with aryldiazonium chlorides, benzaldehyde, formamide, phosphorus pentasulphide and sodium azide have been investigated.The quinazolinone (4), obtained by the action of formamide on 1a, reacts with dialkyl sulphate, phosphorus oxychloride, methylmagnesium iodide and ethyl chloroacetate to give 4-alkoxy-2-cyanomethylquinazolines (5a,b), 4-chloro-2-cyanomethylquinazoline (5d), 2-acetonylquinazolin-4(3H)-one (6) and 2-cyanomethyl-4-quinazolyloxyacetic acid ethyl ester (5c), respectively.The ester (5c) on condensation with hydrazine hydrate and amines gives the corresponding amides (5e-g) whereas with benzaldehyde in the presence of NaOEt, it gives 3-(α-benzylidene)cyanomethyl-4-quinazolyloxy(α'-benzylidene)acetic acid ethyl ester (7).However, 5c undergoes Stobbe condensation in the presence of potassium t-butoxide to give 8. 2-Cyanomethyl-3,1-benzothiazine-4(H)-thione (9), obtained by the action of P2S5 on 1a, reacts with Grignard reagents and amines or hydrazine hydrate to give carbinols (10a-d) and thioamides (10e-j) respectively.The thione (9) on heating with copper bronze in xylene gives 4,4'-bi-3,1-benzothiazine>-2,2'-diacetonitrile (11)
