Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 2. Photocyclisation of halogenoacetyl tryptophol derivatives and α-chloro indol-3-ylalkanoate esters

Anthony L. Beck, Mark Mascal, Christopher J. Moody, William J. Coates

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Irradiation of the trichloroacetates 2, 4 and 5, derived from the corresponding tryptophols, in methanolic acetonitrile results in photocyclisation to the indole 4-position, and the formation of the pyrrolobenzoxocines 9-11. Attempted photocyclisation of the 'reversed' α-chloro esters 15a, 15b and 18 was thwarted by readily occurring elimination of HCl, although the dimethyl compound 15c did cyclise to give the cycloheptaindole 20 upon irradiation in acetonitrile.

Original languageEnglish (US)
Pages (from-to)813-822
Number of pages10
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number7
StatePublished - 1992
Externally publishedYes

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Indoles
Esters
Irradiation
Derivatives
tryptophol
acetonitrile
indole

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 2. Photocyclisation of halogenoacetyl tryptophol derivatives and α-chloro indol-3-ylalkanoate esters. / Beck, Anthony L.; Mascal, Mark; Moody, Christopher J.; Coates, William J.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 7, 1992, p. 813-822.

Research output: Contribution to journalArticle

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AU - Moody, Christopher J.

AU - Coates, William J.

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