Science of Synthesis

Gallagher, P. T., Science of Synthesis, (2001) 10, 707.

9-Arylcarbazoles may be synthesized by reacting 1-arylpyrroles with 2,5-dimethoxytetrahydrofuran in glacial acetic acid, in yields ranging from 22 to 55% (‌Scheme 23‌). 1-Phenyl-1H-pyrrole (‌53‌) can be made from aniline (1 equiv) and 2,5-dimethoxytetrahydrofuran (‌54‌).[‌73‌] Mechanistically the reaction in ‌Scheme 23‌ goes via initial condensation of ‌53‌ with ‌54‌ to produce 1-phenylindole. The condensation process is then repeated to produce the 9-phenyl-9H-carbazole (‌55‌). The condensation between 2,5-dimethoxytetrahydrofuran (3 equivs) and aniline (1 equiv) also produces 9-arylcarbazoles, albeit in lower yield.

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