1027821-55-1Relevant articles and documents
Alkanethiol-Mediated Cyclization of o-Alkynylisocyanobenzenes: Synthesis of Bis-Thiolated Indole Derivatives
La-Ongthong, Kannika,Naweephattana, Phiphop,Khaikate, Onnicha,Surawatanawong, Panida,Soorukram, Darunee,Pohmakotr, Manat,Reutrakul, Vichai,Leowanawat, Pawaret,Kuhakarn, Chutima
, p. 6338 - 6351 (2020/07/21)
Reactions of o-alkynylisocyanobenzenes with a variety of alkanethiols (Alk-SH) provide the corresponding bis-thiolated indole derivatives. The advantages of the reaction include metal-free, room-temperature, mild reaction conditions and broad functional group compatibility. The reaction proceeds via nucleophilic addition of an alkanethiol to an isonitrile moiety, 5-exo cyclization, followed by nucleophilic addition of an alkanethiol to a 3-alkylidene indole intermediate. Density functional calculations on the electronic structures and relative free energies of 5-exo and 6-endo cyclization pathways support that the 5-exo cyclization is preferable.
Synthesis of 3-substituted quinolin-2(1H)-ones via the cyclization of o-alkynylisocyanobenzenes
Charoenpol, Ailada,Meesin, Jatuporn,Khaikate, Onnicha,Reutrakul, Vichai,Pohmakotr, Manat,Leowanawat, Pawaret,Soorukram, Darunee,Kuhakarn, Chutima
supporting information, p. 7050 - 7054 (2018/10/17)
A facile synthesis of various functionalized 3-substituted quinolin-2(1H)-ones through Ag(i) nitrate-catalyzed cyclization of o-alkynylisocyanobenzenes is described. The reaction allows rapid and convenient access to 3-substituted quinolin-2(1H)-one scaffolds in moderate to good yields.
Domino Suzuki coupling and condensation reaction: An efficient strategy towards synthesis of phenanthridines
Ghosh, Munmun,Ahmed, Atiur,Singha, Raju,Ray, Jayanta K.
supporting information, p. 353 - 355 (2015/03/05)
A short and convenient hetero-annulation protocol has been developed for the synthesis of substituted phenanthridines via domino Suzuki coupling and condensation between N-(2-iodo-aryl)-formamide derivatives and 2-formylphenylboronic acid in the presence of Pd(OAc)2, Cs2CO3 and PPh3 as catalytic system in dry DMF at 85-90 °C for 6-7 h. The intermediate after Suzuki coupling and deprotection of nitrogen under the same catalytic system, furnishes the corresponding phenanthridines in good yields after immediate condensation and dehydration.
