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Unusual Formation of Cyclopenta[ b]indoles from 3-Indolylmethanols and Alkynes
, Soniya Gandhi
Published in American Chemical Society
2019
PMID: 30852894
Volume: 84
   
Issue: 7
Pages: 3904 - 3918
Abstract
Acid-promoted synthesis of cyclopenta[b]indole frameworks from 3-indolylmethanols and alkynes has been reported. The overall transformation represents a formal [3 + 2] annulation via rearrangement. This protocol showed good generality for the carbinol substrates as well as alkynes and allowed the generation of structurally diverse cyclopenta[b]indoles. Terminal alkynes, dialkyl-substituted internal alkynes, and alkynes with electron-deficient substituents were found to be not suitable for this transformation. Similarly, N-Ts and N-Boc groups were compatible with reaction conditions, whereas N-Ac and N-Tf failed to undergo this reaction. Isolation of vinyl chloride intermediate suggested the involvement of a vinylic carbocation intermediate. A mechanism has been proposed involving a ring-opening-ring-closing cascade followed by a 1,3-indole migration process via a spirocyclobutene intermediate. © 2019 American Chemical Society.
About the journal
JournalData powered by TypesetJournal of Organic Chemistry
PublisherData powered by TypesetAmerican Chemical Society
ISSN00223263
Open AccessNo
Concepts (57)
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    Chlorine compounds
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    ACID-PROMOTED SYNTHESIS
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    Electron-deficient
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    Internal alkynes
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    MIGRATION PROCESS
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    Reaction conditions
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    Ring closings
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    TERMINAL ALKYNE
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    VINYL CHLORIDES
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    Hydrocarbons
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    1 (4 FLUOROPHENYL) 3 METHYL 2 PHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    1 (4 TERT BUTYLPHENYL) 3 METHYL 2 PHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    1 METHYL 4 TOSYL 3 (1 TOSYL 1H INDOL 3 YL) 1,2,3,4 TETRAHYDROCYCLOPENTA[B]INDOLE
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    1 [3 (4 ACETYL 1 METHYL 1,2,3,4 TETRAHYDROCYCLOPENTA[B]INDOL 3 YL) 1H INDOL 1 YL]ETHAN 1 ONE
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    2 ([1,1' BIPHENYL] 4 YL) 3 METHYL 1 PHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    2 BUTYL 3 METHYL 1 4 TOLYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    2 BUTYL 3 METHYL 1 PHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    2 DECYL 3 METHYL 1 PHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    2,3 DIMETHYL 1 PHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    3 (4 CHLORO 3 METHYLPENT 3 EN 2 YL) 1 TOSYL 1H INDOLE
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    3 (4 CHLORO 3,4 DIPHENYLBUT 3 EN 2 YL) 2 METHYL 1 TOSYL 1H INDOLE
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    3 BUTYL 1,2 DIPHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    3 DECYL 1,2 DIPHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    3 ETHYL 1,2 DIPHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    3 HEXYL 1,2 DIPHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    3 INDOLEMETHANOL
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    3 METHYL 1,2 DIPHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    3 METHYL 1,2,7 TRIPHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    3 METHYL 2 OCTYL 1 4 TOLYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    3 METHYL 2 PHENYL 1 4 TOLYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    3 METHYL 2 PHENYL 4 TOSYL 1 [3 (TRIFLUOROMETHYL)PHENYL] 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    3 OCTYL 1,2 DIPHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    6 BROMO 3 METHYL 1,2 DIPHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    7 BROMO 3 METHYL 1,2 DIPHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    8 BROMO 3 METHYL 1,2 DIPHENYL 4 TOSYL 3,4 DIHYDROCYCLOPENTA[B]INDOLE
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    Alkyne derivative
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    Cyclopentane derivative
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    Indole derivative
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    TERT BUTYL 3 METHYL 1,2 DIPHENYLCYCLOPENTA[B]INDOLE 4(3H) CARBOXYLATE
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    Unclassified drug
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    Unindexed drug
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    Annulation reaction
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    Aromatization
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    Article
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    Cyclization
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    Cycloaddition
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    Drug design
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    Drug structure
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    Drug synthesis
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    Isomer
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    Nuclear overhauser effect
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    Reaction optimization
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    Reaction temperature
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    Reaction time
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    Ring opening
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    Sonogashira reaction
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    X ray diffraction