Vélez Del Burgo Ander, Ochoa de Retana Ana M, de Los Santos Jesús M, Palacios Francisco
Departamento de Química Orgánica I, Facultad de Farmacia, Centro de Investigaciones y Estudios Avanzados "Lucio Lascaray", Universidad del País Vasco , Apartado 450, 01080 Vitoria, Spain.
J Org Chem. 2016 Jan 4;81(1):100-8. doi: 10.1021/acs.joc.5b02347. Epub 2015 Dec 17.
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-α-aminoalkyl phosphine oxides 12, involving the carbonyl group and the Cα 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.
环戊并[b]-吡咯-2-膦氧化物4a和膦酸酯4b、c是通过将源自2-氧代环戊烷羧酸乙酯2的环状烯醇盐加成到膦化的2H-氮杂环丙烷1上生成的。然而，将源自无环2-氧代丁酸酯10的烯醇盐加成到2H-氮杂环丙烷膦氧化物1上会生成乙烯型N-酰基-α-氨基烷基膦氧化物12，涉及羰基和酮酯10的Cα。在碱存在下乙烯型衍生物12的环化反应得到吡咯-2-膦氧化物11。将源自茚满酮羧酸酯15的烯醇盐加成到2H-氮杂环丙烷1上会导致形成官能化的N-取代的1H-苯并[d]氮杂卓衍生物17。
