Methoxylation of bromo-1,2,3,4-tetrahydrocarbazoles. Oxidation and subsequent rearrangement of 1,2,3,4-tetrahydrocarbazoles to spiro(cyclopentane-1,2'-indolin)-3'-ones.
Year: 1981
Type: article
Abstract: 5-Bromo- and 7-bromo-1, 2, 3, 4-tetrahydrocarbazoles (2 and 4) were converted to 4'-methoxy- and 6'-methoxy-spiro (cyclopentane-1, 2'-indolin)-3'-ones (14 and 16) by treatment with excess sodium methoxide in methanol/DMF in the presence of cuprous iodide in 10.3% and 53.7% yields, respectively. On the other hand, N-substituted bromocarbazoles were converted to the corresponding methoxycarbazoles in good yields under the same reaction conditions.
DOI: 10.1248/cpb.29.1231
Authors: YASUO KIKUGAWA, YUKO MIYAKE, MASAMI KAWASE
Institution: Josai University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W1590213499