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Paper | Regular issue | Vol 36, No. 7, 1993, pp.1641-1644
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6379
A One-Step Synthesis of 2,3-Diydro-1,4-benzothiazines and Phenothiazines from 1,3-Thiazolidine Derivatives of Cyclohexanones

Romualdo Caputo, Carla Ferreri,* Luigi Longobardo, Domenico Mastroianni, Giovanni Palumbo,* and Silvana Pedatella

*Dipartimento di Chimica Organica e Biologica, Università di Napoli "Federico II", Via Mezzocannone 16, I-80134 Napoli, Italy


N-Acetyl-1,3-thiazolidine derivatives of cyclohexanones, when treated with a threefold excess N-bromosuccinimide in anhydrous chloroform at room temperature, smoothly afford N-acetyl-2,3-dihydro-1,4-benzothiazines. This represents the first general route to such heterocyclic system in one step from aliphatic precursors. The synthesis of optically active N-acetyl-2,3-dihydro-1,4-benzothiazines is also reported.