1-(2-Aminophenyl)pent-1-yne 1 reacted with benzenethiol at 150 OC 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. (C) 1998 Elsevier Science Ltd. All rights reserved.
Sulfanyl radical mediated cyclization of aminyl radicals
Navacchia ML
1998
Abstract
1-(2-Aminophenyl)pent-1-yne 1 reacted with benzenethiol at 150 OC 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. (C) 1998 Elsevier Science Ltd. All rights reserved.File in questo prodotto:
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