1. Reaction of 2H-Azirine-Phosphine Oxides and -Phosphonates with Enolates Derived from β-Keto Esters.
- Author
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del Burgo, Ander Vélez, de Retana, Ana M. Ochoa, de los Santos, Jesús M., and Palacios, Francisco
- Subjects
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CHEMICAL reactions , *CYCLOPENTANE derivatives , *CYCLOPOLYMERIZATION , *PHOSPHINE oxides , *PHOSPHONATES , *KETONIC acids , *AZIRINES - 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]
- Published
- 2016
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