C. Sha, K. Chuang, Shiow‐Jyi Wey
1987
Citations
0
Influential Citations
23
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
The 2,4-dihydropyrrolo[3,4-b]indole (5) was prepared by the intramolecular 1,3-dipolar cycloaddition of the azidoalkylidenemalonate (11), followed by 1,3-dipolar cycloreversion of the triazoline intermediates (12). Diels–Alder reaction of 2,4-dihydropyrrolo[3,4-b] indole derivative (6) with reactive dienophiles, such as N-phenylmaleimide, benzyne, and dimethyl acetylenedicarboxylate, gave the corresponding cycloadducts (15) and (16), (17), and (20) respectively. Arenimine (17) could be treated with lithium–ammonia to afford the dihydrobenzocarbazole (18), which was dehydrogenated by DDQ to give the benzocarbazole (19).