Efficient synthesis of benzothiazine and acrylamide compounds

• Main Author: Souza,Ana Maria Alves
• Publication Date: 2010
• Other Authors: Walfrido,Simone Torres Pádua, Leite,Lúcia Fernanda Costa, Lima,Maria Carmo Alves, Galdino,Suely Lins, Pitta,Ivan Rocha, Barbosa Filho,José Maria, Simone,Carlos Alberto De, Ellena,Javier Alcides
• Format: Article
• Language: eng
• Source: Química Nova (Online)
• Download full: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422010000300013
• topic: benzothiazines; acrylamides; X-ray crystallography

This article describes the synthesis of the new (2Z)-2-(4-methoxybenzylidene)-6-nitro-4H -benzo[1,4]thiazin-3-one, (2Z)-2-(4-methoxybenzylidene)-4-methyl-6-nitro-4H-benzo[1,4]thiazin-3-one, (2Z)-6-amino-2-(4-methoxybenzylidene)-4H -benzo[1,4]thiazin-3-one, (2Z)-6-butylamino-2-(4-methoxybenzylidene)-4-methyl-4H-benzo[1,4]-thiazin-3-one and (2E)-N-alkyl-N-(2-hydroxy-5-nitrophenyl)-3-phenylacrylamides and the spectroscopic data. The arylidenebenzothiazine compounds were prepared using the Knoevenagel condensation with substituted benzaldehydes in the presence of sodium methoxide in DMF. The presence of a nitro substituent in the 4-position, water and a slightly acid reaction medium in this condensation caused the rupture of the benzothiazine ring and subsequent formation of the phenylacrylamide compounds. A crystallographic data was presented for (2E)-3-(4-bromophenyl)-N-dodecyl-N -(2-hydroxy-5-nitrophenyl) acrylamide.