Issue 14, 2005
From the journal:

Organic & Biomolecular Chemistry

3-Mercaptopropionic acid–nitrile imine adducts. An unprecedented cyclization into 1,3,4-thiadiazol-2(3H)-ones and -2(3H)-thiones

Jalal A. Zahra,a   Bassam A. Abu Thaher,b   Mustafa M. El-Abadelah*a  and  Roland Boesec  

* Corresponding authors

a Chemistry Department, Faculty of Science, University of Jordan, Amman, Jordan
E-mail: mustelab@ju.edu.jo
Fax: 00962 6 534 8932

b Chemistry Department, Faculty of Science, Islamic University of Gaza, Gaza Strip

c Institut für Anorganische Chemie, Universität Duisburg-Essen, Campus Essen Universitätstrasse 3–5, Essen, Germany

Abstract

3-Mercaptopropionic acid–nitrile imine acyclic adducts (6a–c) undergo cyclocondensation with 1,1′-carbonyldiimidazole to afford the respective 1,3,4-thiadiazol-2-(3H)-ones (7a–c). Corresponding 1,3,4-thiadiazol-2(3H)-thiones (8a–c) were likwise produced from 6a–c and 1,1′-thiocarbonyldiimidazole, with consequent elimination of the propionate moiety. The constitution of these heterocyclic products follows from analytical and spectral data and is confirmed by single crystal X-ray structure determination for 7b.

Graphical abstract: 3-Mercaptopropionic acid–nitrile imine adducts. An unprecedented cyclization into 1,3,4-thiadiazol-2(3H)-ones and -2(3H)-thiones

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B505010C
Article type
Paper
Submitted
12 Apr 2005
Accepted
13 May 2005
First published
13 Jun 2005

Org. Biomol. Chem., 2005,3, 2599-2603

Permissions

Request permissions

3-Mercaptopropionic acid–nitrile imine adducts. An unprecedented cyclization into 1,3,4-thiadiazol-2(3H)-ones and -2(3H)-thiones

J. A. Zahra, B. A. Abu Thaher, M. M. El-Abadelah and R. Boese, Org. Biomol. Chem., 2005, 3, 2599 DOI: 10.1039/B505010C

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.

Social activity

Spotlight

Advertisements