1H-1,3-benzazaphospholes: The organometallic route and a new three-step synthesis, with reductive ring closure

Authors
Bansal, RK Gupta, N Heinicke, J Nikonov, GN Saguitova, F Sharma, DC
Citation
Rk. Bansal et al., 1H-1,3-benzazaphospholes: The organometallic route and a new three-step synthesis, with reductive ring closure, SYNTHESIS-S, (2), 1999, pp. 264-269
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
2
Year of publication
1999
Pages
264 - 269
Database
ISI
SICI code
0039-7881(199902):2<264:1TORAA>2.0.ZU;2-M
Abstract
Primary and N-secondary 2-phosphanylanilines were synthesized via metallati on of 2-bromoanilines, coupling with CIP(NMe2)(2) alcoholysis and reduction with LiAlH4, and subsequently reacted with formimidoester hydrochloride to give 1,3-benzazaphospholes. For 1H-1,3-benzazaphospholes, a shorter altern ative three-step synthesis was developed, based on N-acylation of 2-bromoan iline, NiCl2-catalyzed arylation of triethyl phosphite and a new reductive cyclization of amidophosphonic acid ester with excess LiAlH4.