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15.5.1.1.1.5.2.2 Method 2: From N-Substituted N′-(1,2-Diarylvinyl)carbodiimides

DOI: 10.1055/sos-SD-015-01146

Álvarez, M.; Joule, J. A.Science of Synthesis, (200515725.

Isoquinolin-1-amines 235 are formed by the electrocyclization of carbodiimides 233 followed by rearomatization of the initial product, 234 (Scheme 106).[‌212‌] The carbodiimide intermediates 233 can be formed most conveniently by aza-Wittig condensation between an isocyanate and an α,β-unsaturated iminophosphorane; the latter are themselves available[‌213‌] from the reaction of a nitrile with [(triphenylphosphoranylidene)methyl]arene. The reaction can also be performed by combination of the α,β-unsaturated iminophosphorane 236 with the isocyanate without isolation of the carbodiimide to give the iso­quin­oline 237 (Scheme 106).[‌214‌]

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