N-Oxide-Induced Ugi Reaction: A Rapid Access to Quinoline-C2-amino Amides via Deoxygenative C(sp2)-H Functionalization

被引：5

作者：

Anugu, Naveenkumar ^{[1
]}

Thunga, Sanjeeva ^{[1
]}

Poshala, Soumya ^{[1
]}

Kokatla, Hari Prasad ^{[1
]}

机构：

[1] Natl Inst Technol Warangal, Dept Chem, Warangal 506004, Telangana, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 15期

关键词：

MULTICOMPONENT REACTIONS; SMILES COUPLINGS; ISONITRILE; REARRANGEMENT; ISOCYANIDES; COMPLEXITY; TETRAZOLES; CHEMISTRY; ARYLATION; MILD;

D O I：

10.1021/acs.joc.2c00904

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A logic-based replacement of the carboxylic acid component of the Ugi reaction by quinoline N-oxides has been developed. In this approach, the carboxylic isostere, quinoline N-oxide, plays a vital role by shifting the equilibria toward the product side with irreversible addition onto the C2-position of the N-oxide. Thus, aldehydes react with amines, isocyanides, and quinoline N-oxides to furnish quinoline four-component Ugi adducts. The unique reactivity of N-oxides with Ugi components opens an efficient synthetic route for the preparation of biologically active compounds.

引用

页码：10435 / 10440

页数：6

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