An efficient synthesis of 2-alkyl-4-hydroxy-2H-1,2-benzothiazine-3- carboxamide-1,1-dioxides

被引：0

作者：

机构：

[1] Applied Chemistry Research Center, PCSIR Laboratories Complex, Lahore

[2] Institute of Chemistry, University of the Punjab, Lahore

来源：

Zia-ur-Rehman, M. (rehman_pcsir@hotmail.com) | 1771年 / Korean Chemical Society卷 / 26期

关键词：

1,2-Benzothiazine-3-carboxamide; Ionic liquid; Meloxicam; N-Alkylation; Piroxicam;

D O I：

10.5012/bkcs.2005.26.11.1771

中图分类号：

学科分类号：

摘要：

An efficient and environment friendly method has been described for the synthesis of various 2-alkyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1- dioxides starting from N-alkylation of sodium o-benzosulfimide in an ionic liquid for the first time. Ring cleavage and ring closure of the resulting product were achieved in a single step in a cost effective solvent (methanol) followed by N-alkylation of resulting alkyl 4-hydroxy-2H-1,2-benzothiazine-3- carboxylate in ionic liquid while boron triflouride was used as a catalyst along with molecular sieves in carboxamide formation step.

引用

页码：1771 / 1775

页数：4

共 29 条

[1] Hanson P.R., Probst D.A., Robinson R.E., Yau M., Tetrahedron Lett., 40, (1999)
[2] Moree W.J., Van Der Marel G.A., Liskamp R.M., Tetrahedrn Lett., 32, (1991)
[3] Rough W.R., Gwaltney S.L., Cheng J., Scheidt K.A., Mc Kerrow J.H., Hansell E., J. Am. Chem. Soc., 120, (1998)
[4] Ahn K.H., Ham C., Kim S.-K., Cho C.-W., J. Org. Chem., 62, (1997)
[5] Oppolzer W., Kingma A.J., Pillai S.-K., Tetrahedrn Lett., 32, (1991)
[6] Gennarti C., Salom B., Potenza D., Williams A., Angew. Chem. Int. Ed. Engl., 33, (1994)
[7] Lombardino J.G., Wiseman E.H., Mclamore W., J. Med. Chem., 14, (1971)
[8] Braun J., Chem. Ber., 56, (1923)
[9] Abe K., Yammamoto S., Matsui K., Yakagaku Zasshi, 76, (1956)
[10] Soler J.E.

← 1 2 3 →