96325-51-8Relevant articles and documents
Heterocyclic β-Enamino Esters, 36. The Cycloaddition-Ring Enlargement Principle on 4,5-Dihydropyrroles: 6,7-Dihydro-1H-azepines, Pyrimidoazepines, and 1,2,4-Triazolopyrimidoazepine
Wamhoff, Heinrich,Hendrikx, Georg
, p. 863 - 872 (2007/10/02)
The 2-amino-1-tosyl-Δ2-pyrroline enamino esters 2a,b react with dichlorotriphenylphosphorane to give the iminophosphoranes 3a,b.With acetylenic esters (4a-c) the 6,7-dihydro-1H-azepines 6a-d are formed according to the cycloaddition-ring enlargement principle.Acids hydrolyze to afford the free azepine enamino esters 7a,c,d.With phenyl isocyanate 6a gives the carbodiimide 9, which upon treatment with 5percent aq.NaOH cyclizes to give the pyrimidoazepine 10.Analogously, isopropylamine and hydrazine lead to the 2-N-substituted bicycles 11a,b; with triethyl orthoformiate 11a yields the novel 5:6:7-tricycle 13.