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Reaction of Spiro[1,3-benzodioxole-benzothiazines] with Hydroxylamine and Active Methylene Compounds by N. Latif; I. F. Zeid; N. Mishriky; F. M. Assad is a Chemistry article available to read on EtoBox.

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## Abstract The reactivity of the title spiranes (**1**) towards cleavage by different nucleophiles in ethanolic solutions has been investigated. The spiranes are cleaved by ethyl __p__‐aminobenzoate to give 2‐aryl‐3‐(4‐methoxycarbonylphenyl)‐3__H__‐quinazoline‐4‐thiones (**2b–d**) together with tetrachlorocatechol, in a manner similar to the reaction with anilines and hydrazines. However, cleavage with hydroxylamine in ethanol affords ethyl 2‐(thioaroylamino)benzoates (**4**) in addition to the expected 2‐aryl‐3‐hydroxy‐3__H__‐quinazoline‐4‐thiones (**2e‐f**). In contrast to the situation found with amines and hydrazines, the spiranes give 4‐(dicyanomethylene)‐and 4‐[cyano(ethoxycarbonyl)methylene]‐2‐aryl‐3,1‐benzothiazines (**5**) along with the 2‐(thioaroylamino)benzoates (**4**) when reacted with malononitrile and with ethyl cyanoacetate. In all cases, tetrachlorocatechol is produced. Reaction pathways are discussed.

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Author

N. Latif; I. F. Zeid; N. Mishriky; F. M. Assad

Publisher

Elsevier Science; Wiley (John Wiley & Sons); Royal Netherlands Chemical Society; Wiley (ISSN 0165-0513)

Published

2010

Language

EN

Field

Chemistry (Physical Sciences)