Sulfanyl radical mediated cyclization of aminyl radicals

1-(2-Aminopheny)pent-1-yne 1 reacted with benzenethiol at 150 °C under radical conditions to give the thiol alkyne adduct 2, the benzothiophene 4 and the indole 5. Reaction of 1 with benzenesulfanyl radicals produced from diphenyl disulfine in the absence of hydrogen donors gave only the indole 5 in...

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Bibliographic Details
Published inTetrahedron letters Vol. 39; no. 49; pp. 9077 - 9080
Main Authors Montevecchi, Pier Carlo, Navacchia, Maria Luisa
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.12.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Radicals and Radical Reactions. Cyclisation. Alkynes. Amines
Science & Technology
Radicals and Radical Reactions. Cyclisation. Alkynes. Amines
radicals and radical reactions
ACTIVATION
alkynes
amines
cyclisation
ENERGIES
PRECURSORS
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Summary:1-(2-Aminopheny)pent-1-yne 1 reacted with benzenethiol at 150 °C under radical conditions to give the thiol alkyne adduct 2, the benzothiophene 4 and the indole 5. Reaction of 1 with benzenesulfanyl radicals produced from diphenyl disulfine in the absence of hydrogen donors gave only the indole 5 in high yields. Formation of indole 5 was explained in terms of sulfanyl radical mediated aminyl radical cyclization onto the alkyne triple bond. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)01998-4