Diazo Glutaconimides: an Unexplored Type of Heterocyclic α‐Diazocarbonyl Compounds Conveniently Evolved into Pyridine‐2,6(1H,3H)‐diones and Oxazolo[5,4‐b]pyridin‐5(4H)‐ones

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...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-01, Vol.2021 (4), p.623-631
Main Authors: Guranova, Natalia, Kantin, Grigory, Dar'in, Dmitry, Krasavin, Mikhail
Format: Article
Language:English
Subjects:
[3+2] Cycloaddition
Diazo glutaconimides
Diazo transfer
Oxazolo[5,4-b]pyridines
Rh(II) catalysis
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Summary: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(1H,3H)‐diones and oxazolo[5,4‐b]pyridin‐5(4H)‐ones via a Rh2(esp)2‐catalyzed XH‐insertion reaction and [3+2] cycloaddition with nitriles, respectively. The newly synthesized 1,4‐disubstituted α‐diazo glutaconimides are converted into polysubstituted pyridines and oxazolo[5,4‐b]pyridine via the reactions of Rh(II)‐catalyzed XH‐insertion and [3+2] cycloaddition to nitriles, respectively.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202001451