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Synthesis 1999; 1999(2): 264-269
DOI: 10.1055/s-1999-3394
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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
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Publication Date:
31 December 1999 (online)

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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

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