Phosphorylation of imidazo[2,1-b]thiazoles with phosphorus(III) halides in the presence of bases
✍ Scribed by Evgenij V. Zarudnitskii; Aleksandr A. Yurchenko; Anatolij S. Merkulov; Marina G. Semenova; Aleksandr M. Pinchuk; Andrej A. Tolmachev
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- English
- Weight
- 114 KB
- Volume
- 16
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.20166
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
The reaction of phosphorus(III) halides with 6‐substituted imidazo[2,1‐b]thiazoles in the presence of bases proceeds regioselectively and affords 5‐phosphinoimidazo[2,1‐b]thiazoles, useful synthons for the preparation of various P(III) and P(V) derivatives. 5‐Phosphinoimidazo[2,1‐b]thiazoles are selectively alkylated at the phosphorus or heterocyclic nitrogen atom, depending on the alkylating agent. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:648–655, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20166
📜 SIMILAR VOLUMES
Phosphorylation of 1-alkyl substituted imidazoles and benzimidazoles with P(III) halides in pyridine was shown to proceed at the 3-N atom of the heteroaryl ring and was followed by triethylamine-induced migration of the phosphorus group to the 2-C atom. Preparative methods were developed for the syn
## Abstract 2‐(3‐Methyl‐1,3‐diazabuten‐1‐yl)‐3‐ethoxycarbonylthiophenes are phosphorylated with phosphorus(III) halides in basic media at position 5 of the thiophene ring. Up to three heteroaromatic substituents can be introduced one by one at the same phosphorus atom. On this basis, mono‐, bis‐, a