One-pot regioselective synthesis of n-benzoyl 2-amino-3,4-dihydro-3-oxo-2h-1,4-benzothiazines

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One-pot regioselective synthesis of n-benzoyl 2-amino-3,4-dihydro-3-oxo-2h-1,4-benzothiazines

E. Mabrouk¹, A. Elachqar¹, A. Alami¹*, A. El Hallaoui¹ and S. El Hajji¹

¹Laboratoire de Chimie Organique, Faculté des Sciences Dhar El Mehraz, Université Sidi Mohamed Ben Abdellah,B.P. :1796-Fès Atlas, Fès, Maroc. ²Laboratoire des Aminoacides, Peptides et Protéines (LAPP), UMR5810-CNRS, Université Montpellier II, France.

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ABSTRACT:

A protocol for regioselective one-pot synthesis of 2-amino-3,4-dihydro-3-oxo-2H-1,4- benzothiazines has been developed. Starting from commercially available 2-aminothiophenols, a basemediated regioselective S-alkylation took place with methyl α-azido glycinates to give the acyclic intermediates, which underwent spontaneously an intramolecular amidation reaction to furnish 2-amino- 3,4-dihydro-3-oxo-2H-1,4-benzothiazines in 68% yields.

KEYWORDS:

amino acids; methyl α-azido glycinate; 2-aminothiophenol; S-alkylation; N-alkylation; N-benzoyl 2-amino-3;4-dihydro-3-oxo-2H-1;4-benzothiazines