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The rhodium-catalyzed reactions of 3-diazoindolin-2-imines with furans and dihydrofuran furnished 9H-pyrido[2,3-b]indoles and tetrahydrofuro[3',2':4,5]pyrrolo[2,3-b]indoles, respectively. A cascade reaction mechanism involving an α-imino rhodium carbene intermediate is proposed. The starting materials are readily available, and the procedure is facile and efficient.

A novel and convenient preparation of 4-diazoisochroman-3-imines through the copper(i)-catalyzed cascade reaction of (2-ethynylphenyl)-methanols with sulfonyl azides is described. The synthesized cyclical α-diazo imidates could readily react with a variety of primary amines to furnish 3-substituted 3,5-dihydroisochromeno[3,4-d][1,2,3]-triazoles under catalyst-free conditions. [ABSTRACT FROM AUTHOR]

The title substrates are transformed into α-imino rhodiumcarbene intermediates which react with furans or tetrahydrofurans to give pyridoindoles and tetrahydrofuropyrroloindoles, respectively. [ABSTRACT FROM AUTHOR]