A new approach to (Z)-3-benzylidene- and 3-ethylidene-2,3-dihydro-2-methyl- 1,2-benzothiazin-4-one 1,1-dioxides (4) starting from the corresponding 3-acyl derivatives (1) is described. A hypothesis, based on 13C n.m.r. data, that products (4) may be considered as α,β-unsaturated carbonyl systems is confirmed experimentally by their chemical behaviour. Reaction with various nucleophiles such as hydrazine, sulphur ylides, and enamines leads to formation of polynuclear heterocyclic systems containing the 1,2-benzothiazine 1,1-dioxide skeleton.

Synthesis, structure and reactivity to nucleophiles of 3-benzylidene and 3-ethylidene-2,3-dihydro-2-methyl-1,2-benzothiazin-4-one 1,1-dioxides / P. Dalla Croce, D. Del Monaco, C. La Rosa. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - (1986), pp. 299-302.

Synthesis, structure and reactivity to nucleophiles of 3-benzylidene and 3-ethylidene-2,3-dihydro-2-methyl-1,2-benzothiazin-4-one 1,1-dioxides

P. Dalla Croce
Primo
;
C. La Rosa
Ultimo
1986

Abstract

A new approach to (Z)-3-benzylidene- and 3-ethylidene-2,3-dihydro-2-methyl- 1,2-benzothiazin-4-one 1,1-dioxides (4) starting from the corresponding 3-acyl derivatives (1) is described. A hypothesis, based on 13C n.m.r. data, that products (4) may be considered as α,β-unsaturated carbonyl systems is confirmed experimentally by their chemical behaviour. Reaction with various nucleophiles such as hydrazine, sulphur ylides, and enamines leads to formation of polynuclear heterocyclic systems containing the 1,2-benzothiazine 1,1-dioxide skeleton.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/193625
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