Domino Reaction of Isatins with α‐Oxoketene‐N,S‐acetals: An Efficient Synthesis of Pyrrolo[3,4‐c]quinoline‐1,3‐diones and 2,3‐Dihydro‐1H‐pyrrolo[3,4‐c]quinolin‐1‐ones

A straightforward synthesis of pyrrolo[3,4‐c]quinoline‐1,3‐diones and 2,3‐dihydro‐1H‐pyrrolo[3,4‐c]quinolin‐1‐ones has been accomplished by the cascade reaction of isatins with α‐oxoketene‐N,S‐acetals using BF3 ⋅ Et2O in DMSO/toluene at 110 °C. The reaction offers an easy access to biologically impo...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2021-11, Vol.10 (11), p.2964-2968
Main Authors: Sharma, Anup Kumar, Jaiswal, Anjali, Chand, Shiv, Singh, Krishna Nand
Format: Article
Language:English
Subjects:
2,3-Dihydro-1H-pyrrolo[3,4-c]quinolin-1-ones
BF3 ⋅ Et2O
Isatins
Ketene N,S-acetals
Pyrrolo[3,4-c]quinoline-1,3-diones
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Summary:A straightforward synthesis of pyrrolo[3,4‐c]quinoline‐1,3‐diones and 2,3‐dihydro‐1H‐pyrrolo[3,4‐c]quinolin‐1‐ones has been accomplished by the cascade reaction of isatins with α‐oxoketene‐N,S‐acetals using BF3 ⋅ Et2O in DMSO/toluene at 110 °C. The reaction offers an easy access to biologically important tricyclic N‐heterocycles via C−C/C−X bond formation. Pyrrolo[3,4‐c]quinoline‐1,3‐diones and 2,3‐dihydro‐1H‐pyrrolo[3,4‐c]quinolin‐1‐ones have been efficiently accomplished by the domino reaction of isatins with α‐oxoketene‐N,S‐acetals using BF3 ⋅ Et2O in DMSO/toluene at 110 °C.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202100489