Structure determination of the products from the acid-catalyzed condensation of indole with acetone

Wayland E Noland, Michael J. Konkel, Lisa M.C. Konkel, Bradley C. Pearce, Charles L. Barnes, Elmer O. Schlemper

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10 Scopus citations

Abstract

Four of the previously reported compounds obtained from the acid-catalyzed condensation of indole with acetone are now assigned the following structures: cis-4,4a,9,9a-tetrahydro-2-(1H-indol-3-yl)-4,4-dimethyl-3H-carbazole (2a), 1,1',4,4'-tetrahydro-1,1,1',1'-tetramethyl-3,3'(2H,2'H)-spirobi[cyclop ent[b]indole] (4), 4,4a-dihydro-2-(3-1H-indolyl)-4,4-dimethyl-3H-carbazol-4a-ol (7), and 5-(2-aminophenyl)-1,3,4,5-tetrahydro-1,1,4,4-tetramethylcyclopent[kl]a cridine (8). The structure of the novel rearrangement product 8 was solved by an X-ray crystal structure determination. The two previously reported autoxidation products of 4 are now assigned the following structures: 1,3',4,4'-tetrahydro-1,1,4',4'-tetramethyl-cis-dispiro[cyclopent[b]ind ole-3(2H),2'(5'H)-furan-5',3''-[3H]-indol]2''(1''H)-one (5) and 1,4-dihydro-1,1,5',5'-tetramethylspiro[cyclopent[b]indole-3(2H),3'(4'H )-1-benzazocine]-2'(1'H),6'(5'H)-dione (6).

Original languageEnglish (US)
Pages (from-to)451-454
Number of pages4
JournalJournal of Organic Chemistry
Volume61
Issue number2
DOIs
StatePublished - Jan 26 1996

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