TY - JOUR

T1 - Novel synthesis of 2,3-dihydrobenzofuran-3-amines from salicylic aldehydes: Trimethylsilyl as traceless activating group

AU - Khardina, Polina a.

AU - Buev, Evgeny m.

AU - Moshkin, Vladimir s.

AU - Sosnovskikh, Vyacheslav y.

N1 - This work was financially supported by the Russian Science Foundation (Grant 22-73-10008).

PY - 2024/4/1

Y1 - 2024/4/1

N2 - Salicylic aldehydes were readily alkylated with (chloromethyl)trimethylsilane to give silylated ortho-methoxy benzaldehydes in 85–96 % yields. These aldehydes were converted into alkyl and aryl imines in excellent yields. O-(Trimethylsilyl)methyl moiety was applied as the synthetic equivalent of aryloxymethyl anion in the nucleophilic cyclization at the imine group promoted by CsF in DMF at 140 °C. Using this traceless methodology, 2,3-dihydrobenzofuran-3-amines were synthesized from salicylic aldehydes in 25–55 % yields in three steps.

AB - Salicylic aldehydes were readily alkylated with (chloromethyl)trimethylsilane to give silylated ortho-methoxy benzaldehydes in 85–96 % yields. These aldehydes were converted into alkyl and aryl imines in excellent yields. O-(Trimethylsilyl)methyl moiety was applied as the synthetic equivalent of aryloxymethyl anion in the nucleophilic cyclization at the imine group promoted by CsF in DMF at 140 °C. Using this traceless methodology, 2,3-dihydrobenzofuran-3-amines were synthesized from salicylic aldehydes in 25–55 % yields in three steps.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85188009638

U2 - 10.1016/j.tetlet.2024.154992

DO - 10.1016/j.tetlet.2024.154992

M3 - Article

VL - 139

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

M1 - 154992

ER -