Microwave‐Assisted and Base‐Promoted Domino Reaction of Cyclic N‐Sulfonyl Ketimines with α,β‐Disubstituted Nitroalkenes: A Green Access to 2‐Hydroxyarylpyridines

Microwave‐assisted and organobase‐promoted eco‐friendly one‐pot protocol has been developed to construct an interesting class of pyridyl‐substituted phenols/α‐naphthols containing a carboxylate or aroyl group at C2 position on the pyridine ring. A series of N‐sulfonyl ketimines and different kinds o...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2018-09, Vol.7 (9), p.1810-1814
Main Authors: Guin, Soumitra, Majee, Debashis, Biswas, Soumen, Samanta, Sampak
Format: Article
Language:English
Subjects:
2-hydroxyarylpridines
Acetates
Cascade chemical reactions
domino method
Imines
MBH acetates of nitroalkenes
microwave irradiation
Organic chemistry
organobase
Phenols
α-arylacetylenyl-β-arylnitroolefins
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Summary:Microwave‐assisted and organobase‐promoted eco‐friendly one‐pot protocol has been developed to construct an interesting class of pyridyl‐substituted phenols/α‐naphthols containing a carboxylate or aroyl group at C2 position on the pyridine ring. A series of N‐sulfonyl ketimines and different kinds of bielectrophiles, such as MBH acetates of nitroalkenes/α‐arylacetylenyl‐β‐arylnitroolefins, were involved in this cyclization process, which delivers good to high yields of aforementioned heterocycles and excels with several compatible functionalities. A series of 2‐hydroxyarylpicolinate derivatives have been synthesized from N‐sulfonyl ketimines and MBH acetates of nitroalkenes/α‐arylacetylenyl‐β‐arylnitroolefins as bielectrophiles in 2‐MeTHF irradiated by MW using DABCO as an organobase.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201800298