Abstract:
The oxidation of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[6-methyl-2-(cyclopent-1-enyl)phenyl]carbamate with hydrogen peroxide in methanolic NaOH gave spiro[4H-3,1-benzoxazine-4,1′-cyclopentanes]. On the other hand, ethyl [2-(cyclopent- 1-enyl)phenyl]carbamate reacted with hydrogen peroxide in the presence of acetonitrile and NaOH to give ethyl 3a-hydroxy-2,3,3a,8b-tetrahydrocyclopenta[b]indole-4(1H)-carboxylate, which was dehydrated with polyphosphoric acid to ethyl 2,3-dihydrocyclopenta[b]indole-4(1H)-carboxylate.
Document Type:
Article
Language: English
Citation:
R. R. Gataullin, M. F. Nasyrov, O. V. Shitikova, L. V. Spirikhin, I. B. Abdrakhmanov, “Heterocyclization of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[2-(cyclopent-1-enyl)phenyl]carbamates under the action of hydrogen peroxide”, Mendeleev Commun., 11:5 (2001), 200–201
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https://www.mathnet.ru/eng/mendc4292
https://www.mathnet.ru/eng/mendc/v11/i5/p200
This publication is cited in the following 3 articles:
R. R. Gataullin, “Synthesis of compounds containing a cycloalka[b]indole fragment”, Russ J Org Chem, 45:3 (2009), 321
A. Kh. Fattakhov, I. B. Abdrakhmanov, R. R. Gataullin, “Reactions of N-acetyl- and N-ethoxycarbonyl-2-(1-cycloalken-1-yl)anilines with meta-cloroperbenzoic acid”, Russ J Gen Chem, 78:8 (2008), 1565
Rail R. Gataullin, Marat F. Nasyrov, Ol'ga V. Shitikova, Leonid V. Spirikhin, Il'dus B. Abdrakhmanov, “ChemInform Abstract: Heterocyclization of N‐[2‐(Cyclopent‐1‐enyl)phenyl]acetamides and Ethyl N‐[2‐(Cyclopent‐1‐enyl)phenyl]carbamates under the Action of Hydrogen Peroxide.”, ChemInform, 33:11 (2002)
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