SYNTHESIS OF THE CARBAZOLE ALKALOIDS HYELLAZOLE AND 6-CHLOROHYELLAZOLE AND RELATED DERIVATIVES

We describe a new seven-stage synthesis of the carbazole alkaloids hyellazole and 6-chlorohyellazole, which proceeds via thermal cyclization of the 3-(buta-1,3 dienyl)indoles 7ab and 7bb. prepared from the condensation products of indole-2,3-diones 1a, b and the 3-methyl-4-phenylbut-3-en-2-one 2b. T...

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Published inJournal of the Chemical Society, Perkin Transactions 1 no. 5; pp. 579 - 587
Main Authors BECCALLI, EM, MARCHESINI, A, PILATI, T
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1994
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Organic compounds
Physical Sciences
Physics
Preparations and properties
Science & Technology
Structure of solids and liquids; crystallography
Structure of specific crystalline solids
Alkaloid
Conjugated polyenic compound
Cyclization
Molecular structure
Nitrogen heterocycle
Aromatic compound
Thermal reaction
Tricyclic compound
Experimental study
X ray diffraction
Organic compounds
Crystalline structure
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Summary:We describe a new seven-stage synthesis of the carbazole alkaloids hyellazole and 6-chlorohyellazole, which proceeds via thermal cyclization of the 3-(buta-1,3 dienyl)indoles 7ab and 7bb. prepared from the condensation products of indole-2,3-diones 1a, b and the 3-methyl-4-phenylbut-3-en-2-one 2b. This procedure was also used to prepare related 3-methoxy-1-phenylcarbazole derivatives.
ISSN:0300-922X
2050-8255
1364-5463
DOI:10.1039/p19940000579