Download PDF
Synthesis 1999; 1999(2): 264-269
DOI: 10.1055/s-1999-3394
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

1H-1,3-Benzazaphospholes: The Organometallic Route and a New Three-Step Synthesis with Reductive Ring Closure

Raj K. Bansal* , Neelima Gupta, Joachim Heinicke, George N. Nikonov, Farida Saguitova, Dinesh C. Sharma
  • *Department of Chemistry, University of Rajasthan, Jaipur 302 004, India; Fax +91(1 41)65 27 84
Further Information

Publication History

Publication Date:
31 December 1999 (online)

  PDF Download  Permissions and Reprints All articles of this category

Primary and N-secondary 2-phosphanylanilines were synthesized via metallation of 2-bromoanilines, coupling with ClP(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 alternative three-step synthesis was developed, based on N-acylation of 2-bromoaniline, NiCl2-catalyzed arylation of triethyl phosphite and a new reductive cyclization of amidophosphonic acid este with excess LiAlH4.

C,N-dilithium reagent - phosphanylaniline - amidoarylphosphonate - reductive cyclization - 1,3-benzazaphosphole