Tetrahedron Letters p. 9077 - 9080 (1998)
Update date:2022-09-26
Topics:
Montevecchi, Pier Carlo
Navacchia, Maria Luisa
1-(2-aminophenyl)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 disulfide 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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