Synthesis of 3-methyl-4H-benzo[b][1,4]thiazine-2-carboxylates Using CAN as a Catalyst and Its Conversion Into Guanidines

(E-pub Ahead of Print)

Author(s): Dhanaji V. Jawale, Devendra Wagare, Dinesh L. Lingampalle, Prashant D. Netankar*

Journal Name: Current Organocatalysis


Become EABM
Become Reviewer
Call for Editor

Abstract:

Background: 1,4-benzothiazine carboxylates show wide application in the field of medicinal chemistry. Therefore, we have designed convenient and efficient method for the synthesis of 1,4-benzothiazine carboxylates.

Objective: Synthesis of 1,4-benzothiazine carboxylates and its guanidines by simple and facile method using efficient catalyst.

Method: Derivatives of 1,4-benzothiazine carboxylates were synthesized by cyclocondensing β-keto esters with 2- aminobenzenethiols using CAN as a catalyst at room temperature. 1,4-benzothiazine caboxylate,condensed with guanidine hydrochloride in the presence of sodium methoxide in DMF to obtained new 3-substituted-l-4Hbenzo[b][1,4]thiazine-2-carboxyguanidines (88-91%).

Results: All the products were obtained with good to excellent yields within 40 min. Here, CAN oxidizes aminothiophenol into disulfide and then nucleophilic attack of enolic form of β-ketoesters on the disulphide and 1, 4-benzothiazine acetates, were obtained with good yields.

Conclusion: we have designed convenient and efficient method for the synthesis of 1,4-benzothiazine carboxylates. Most remarkable features of this cyclocondensation such as use of efficient catalyst and non-volatile solvent under mild reaction condition to obtained excellent yield.

Keywords: Guanidine, 1, 4-Benzothiazine, CAN, 4H-benzo[b][1, 4]thiazine-2-carboxyguanidines.

Rights & PermissionsPrintExport Cite as

Article Details

(E-pub Ahead of Print)
DOI: 10.2174/2213337207999201228141906
Price: $95

Article Metrics

PDF: 2