Pergamon
Tetrahedron Letters 40 (1999) 3457 3460
TETRAHEDRON
LETTERS
Synthesis of 1-Phosphono-2-aza-l,3-dienes and their
Conversion into 1-Vinyi-2-phosphonoaziridines.
Christian Stevens]'* Marc Gallant and Norbert De Kimpe
l)epartment qf Organic ("hemist~'. t'aculO; of.tgricultural and. lpplied Biological Sciences,
( "niversity o f Gent, ("oupure Links 653, B-9000 Gent, Belgium.
Received 4 January 1999 accepted 23 February 1999
Abstract
1-Phosphono-2-aza-l.3-dienes were formed by 1.4-dehydrochlorinalion of the corresponding N-(phosphonomethyl)-~-chloroimines,
and reacted smoothl 3 with diazomethane to give l-vinyl-2-phosphonoaziridines © 1999 Elsevier Science Ltd. All rights reserved.
Kc~x~ords: 2-,tzadiene~: Pho.~phonoaziridines; Diazomethane
Organophosphates have played a significant role in agrochemistry dtmng the past decades but
have mostly been abandoned because of their acute toxicity. Recently, a lot of eflbrt has been
devoted to the synthesis of organophosphonates. More specifically, a-aminophosphonates have
been an important research topic because of their analogy to a-amino acids resulting in enzyme
inhibitor activity [1 ]. Heterocyclic analogues of a-amino phosphonates have not been studied in
detail and, therefore, we have been engaged in developing straightforward methodologies for the
synthesis of azaheterocyclic organophosphonates in order to investigate their physiological
properties. Recently, we reported on the synthesis of phosphonylated 2-bromomethylaziridines
121.
Research Leader of the Belgian "'Fonds voor Wetenschappelijk Onderzock - Vlaanderen'" (Fund for Scientific Research - Flanders)
0040-4039/99/$ - see front matter © 1999 Elsevier Science Ltd. All rights reserved.
Pll: S0040-4039(99)00422-0