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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Published in | Tetrahedron letters Vol. 39; no. 49; pp. 9077 - 9080 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
03.12.1998
Elsevier |
Subjects | |
Online Access | Get full text |
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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.
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/S0040-4039(98)01998-4 |