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1, 3-azaphospholo[5, 1-b]thiazolines and benzothiazoles

✍ Scribed by Raj K. Bansal; Ruchi Mahnot; Dinesh C. Sharma; Konstantin Karaghiosoff; Alfred Schmidpeter

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
519 KB
Volume
3
Category
Article
ISSN
1042-7163

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✦ Synopsis

The title compounds 3 and 7 are nouel heterocyclic systems incorporating two-coordinate phosphorus. They are obtained in reasonable to good yields from the condensation of suitable 2-ethyl-3-alkylthiazolinium and -benzothiazolium bromides 2 and 6 with phosphorus trichloride in the presence of triethylamine in an aprotic solvent. Intermediate dichlo rophosphino -su bst it u ted N-ylides can be o bserued or isolated in some cases. From a 2-methyl-3alkylthiazolinium bromide (2a), a 14dichlorophosphino) substituted 1,3-azaphospholo[ 5,l-blthiazoline (4) was obtained.

The chemical shifi of the two-coordinate phosphorus in 1,3-azaphosphole derivatiues clearly re- flects the influence of the heterocyclic system annulated to its 1,5-bond and of the substituents in its 2and 4-positions.

πŸ“œ SIMILAR VOLUMES

1,3-azaphospholo[5,1-a]isoquinolines
1,3-azaphospholo[5,1-a]isoquinolines
✍ Raj K. Bansal; Leena Hemrajani; Neelima Gupta πŸ“‚ Article πŸ“… 1999 πŸ› John Wiley and Sons 🌐 English βš– 218 KB

In a one pot synthesis, 1,3-azaphospholo [5,1-a]isoquinoline (4) was obtained from the reaction of N-(alkoxycarbonylmethyl)isoquinolinium bromide (1) with PCl 3 in the presence of (C 2 H 5 ) 3 N. A crossed reaction confirms the formation of 4 proceeding via a 1,5-electrocyclization. Compound 4 under

Microwave-assisted synthesis and diels–a
Microwave-assisted synthesis and diels–alder reactions of 1,3-azaphospholo[5,1-a]isoquinolines
✍ Raj K. Bansal; Anshu Dandia; Nidhi Gupta; Dheeraj Jain πŸ“‚ Article πŸ“… 2003 πŸ› John Wiley and Sons 🌐 English βš– 76 KB

## Abstract The application of microwave technique has been extended successfully for the first time to the synthesis of a representative class of azaphospholes, viz. 1,3‐bis(alkoxycarbonyl)‐1,3‐azaphospholo[5,1‐__a__]isoquinolines (**__2__**), which occurs rapidly giving higher yields. Stereoselec