A Three-Component Ugi-Type Reaction of N-Carbamoyl Imines Enables a Broad Scope Primary α-Amino 1,3,4-Oxadiazole Synthesis | Zendy

Daniel MatheauRaven | Zendy; Elizabeth Boulter | Zendy; Tatiana Rogova | Zendy; Darren J. Dixon | Zendy

Open Access

A Three-Component Ugi-Type Reaction of N-Carbamoyl Imines Enables a Broad Scope Primary α-Amino 1,3,4-Oxadiazole Synthesis

Author(s) -

Daniel MatheauRaven,

Elizabeth Boulter,

Tatiana Rogova,

Darren J. Dixon

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c02945

Subject(s) - chemistry , isocyanide , ugi reaction , oxadiazole , primary (astronomy) , combinatorial chemistry , amino acid , imine , component (thermodynamics) , scope (computer science) , stereochemistry , molecule , organic chemistry , catalysis , biochemistry , physics , astronomy , computer science , thermodynamics , programming language

A general synthesis of N -protected primary α-amino 1,3,4-oxadiazoles, from N -carbamoyl imines, N -isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids, is described. Featuring an isocyanide addition reaction with N -carbamoyl imines, this efficient three-component Ugi-type reaction was found to be broad in scope with respect to imine, and carboxylic acid coupling partners. Furthermore, the versatility of this method was demonstrated by α-amino 1,2,4-triazole synthesis, the late-stage functionalization of seven drug molecules, and five divergent derivatizations of a primary α-amino 1,3,4-oxadiazole.

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