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A new method for the preparation of the pyrrolo[2,3-b]quinoline ring system involving the sequential formation of the pyridine ring (electrocyclic ring-closure) and the pyrrole (nitrene insertion reaction) rings. This approach is based on the regioselective formation of the iminophosphorane 2 from the bis(azide) 1, followed by aza Wittig reaction with isocyanates and further thermal treatment.
Compounds resulting from the aza-Wittig reaction of iminophosphorane derived from 2-(2-azidoethyl)indole and carbon disulfide, diphenylketene, aldehydes and acyl chlorides undergo ring-closure under acidic, basic and thermal conditions to give either dihydro γ-carbolines ordihydropyrimido[3, 4-a]indoles in a completely regiospecific fashion. The mode of cyclization strongly depends on the cyclizating...
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