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 CrocePrimo
;C. La RosaUltimo
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.
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