Issue 0, 1986

Synthesis of 1,2,4-benzothiadiazines via readily generated iminium ions

Abstract

A general method for the regiospecific synthesis of 1,2,4-benzothiadiazines, which are powerful diuretics and antihypertensive agents, has been developed. The N-arysulphonylprolyl chlorides (5)–(7) reacted instantaneously with silver trifluoromethanesulphonate at room temperature to give the iminium salts (9)–(11) which provided the nitroamines (13)–(15) in quantitative yield. Reductive cyclisation of the nitroamines led to the tetrahydro-1H-pyrrolo[1,2-b][1,2,4]benzothiadiazine 5,5-dioxides (17)–(20) in very good yields. No optimisation of yields was attempted.

Efficient methods for the synthesis of some new substituted N-(nitrobenzenesulphonyl)-pyrrolidinecarboxylic acids (1)–(4), which were not readily available, are also described.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1986, 805-808

Synthesis of 1,2,4-benzothiadiazines via readily generated iminium ions

B. I. Alo, E. A. Adegoke, M. Ligali-Ali and E. K. Adesogan, J. Chem. Soc., Perkin Trans. 1, 1986, 805 DOI: 10.1039/P19860000805

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements