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Diazo Glutaconimides: an Unexplored Type of Heterocyclic α‐Diazocarbonyl Compounds Conveniently Evolved into Pyridine‐2,6(1 H ,3 H )‐diones and Oxazolo[5,4‐ b ]pyridin‐5(4 H )‐ones
Author(s) -
Guranova Natalia,
Kantin Grigory,
Dar'in Dmitry,
Krasavin Mikhail
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001451
Subject(s) - chemistry , diazo , pyridine , cycloaddition , medicinal chemistry , organic chemistry , catalysis , stereochemistry
A convenient general approach towards 1,4‐disubstituted α‐diazo glutaconimides starting from β‐substituted glutaconic acid anhydrides has been developed. It involves condensation with amines and subsequent diazo transfer reaction. This new class of diazocarbonyl heterocycles has been converted into a series of polysubstituted pyridine‐2,6(1 H ,3 H )‐diones and oxazolo[5,4‐ b ]pyridin‐5(4 H )‐ones via a Rh 2 (esp) 2 ‐catalyzed XH‐insertion reaction and [3+2] cycloaddition with nitriles, respectively.