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Reaction of 2H-Azirine-Phosphine Oxides and -Phosphonates with Enolates Derived from β-Keto Esters.

Authors :
del Burgo, Ander Vélez
de Retana, Ana M. Ochoa
de los Santos, Jesús M.
Palacios, Francisco
Source :
Journal of Organic Chemistry. 1/4/2016, Vol. 81 Issue 1, p100-108. 9p.
Publication Year :
2016

Abstract

Cyclopenta[b]-pyrrole-2-phosphine oxides 4a and -phosphonates 4b,c are generated by the addition of cyclic enolates derived from ethyl 2-oxo-cyclopentanecarboxylate 2 to phosphorated 2H-azirines 1. However, the addition of enolate derived from acyclic 2-oxo-butanoate 10 to 2H-azirine phosphine oxide 1 led to vinylogous N-acyl-a-aminoalkyl phosphine oxides 12, involving the carbonyl group and the Ca of the keto ester 10. Ring closure of vinylogous derivative 12 in the presence of base afforded pyrrole-2-phosphine oxide 11. The addition of enolates derived from indenone-carboxylate 15 to 2H-azirines 1 led to the formation of functionalized N-substituted 1H-benzo[d]azepine derivatives 17. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00223263
Volume :
81
Issue :
1
Database :
Academic Search Index
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
112208614
Full Text :
https://doi.org/10.1021/acs.joc.5b02347