TY - JOUR

T1 - Imines with rare α-heteroatom substituted amine components generated in situ via the Staudinger/aza-Wittig tandem reaction and their application in multicomponent reactions

AU - Парамонова, Полина Сергеевна

AU - Елисеев, Илья Александрович

AU - Дарьин, Дмитрий Викторович

AU - Бакулина, Ольга Юрьевна

PY - 2024/1/29

Y1 - 2024/1/29

N2 - A series of structurally diverse α-heteroatom substituted methyl azides (XCH2N3, where X = phthalimidoyl, benzotriazolyl, arylsulfanyl, aryloxy, alkoxy) have been prepared and evaluated for the in situ generation of imines via the Staudinger/aza-Wittig tandem reaction with aldehydes and triphenylphosphine. The obtained imines were successfully introduced into four types of multicomponent reactions: the Staudinger β-lactam synthesis with diazo carbonyl compounds, the Castagnoli-Cushman reaction with cyclic anhydrides, and the Ugi and azido-Ugi reactions with isocyanides and carboxylic acids or TMS-azides. These transformations allowed the preparation of four-to-seven-membered lactams, acyclic bisamides and 5-(aminomethyl)-1-alkyltetrazoles with a complex and previously poorly accessible periphery. Moreover, it was demonstrated that phthalimide derivatives can be deprotected to afford medicinally relevant N-aminomethyl lactams.

AB - A series of structurally diverse α-heteroatom substituted methyl azides (XCH2N3, where X = phthalimidoyl, benzotriazolyl, arylsulfanyl, aryloxy, alkoxy) have been prepared and evaluated for the in situ generation of imines via the Staudinger/aza-Wittig tandem reaction with aldehydes and triphenylphosphine. The obtained imines were successfully introduced into four types of multicomponent reactions: the Staudinger β-lactam synthesis with diazo carbonyl compounds, the Castagnoli-Cushman reaction with cyclic anhydrides, and the Ugi and azido-Ugi reactions with isocyanides and carboxylic acids or TMS-azides. These transformations allowed the preparation of four-to-seven-membered lactams, acyclic bisamides and 5-(aminomethyl)-1-alkyltetrazoles with a complex and previously poorly accessible periphery. Moreover, it was demonstrated that phthalimide derivatives can be deprotected to afford medicinally relevant N-aminomethyl lactams.

UR - https://www.mendeley.com/catalogue/9c700266-90ca-3aee-9a26-2189c5341463/

U2 - 10.1039/d3ob01832f

DO - 10.1039/d3ob01832f

M3 - Article

VL - 22

SP - 1733

EP - 1744

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 8

ER -