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Microwave‐accelerated Conjugate Addition of 2‐Arylindoles to Substituted β‐Nitrostyrenes in the Presence of Ammonium Trifluoroacetate: An Efficient Approach for the Synthesis of a Novel Class of CB1 Cannabinoid Receptor Allosteric Modulators
Author(s) -
Kulkarni Pushkar M.,
Ranade Ameya,
Garai Sumanta,
Thakur Ganesh A.
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2861
Subject(s) - conjugate , chemistry , trifluoromethanesulfonate , microwave irradiation , combinatorial chemistry , ammonium , cannabinoid , microwave , electrophile , reactivity (psychology) , microwave heating , cannabinoid receptor , medicinal chemistry , organic chemistry , catalysis , receptor , biochemistry , medicine , mathematical analysis , physics , mathematics , alternative medicine , pathology , quantum mechanics , agonist
2‐Arylindoles, in general, exhibit reduced reactivity towards the conjugate addition to substituted nitrostyrenes, when compared with indoles. We report here an efficient, expeditious, and high‐yielding conjugate addition of 2‐arylindoles to substituted β‐nitrostyrenes in the presence of ammonium trifluoroacetate under microwave irradiation. This method is mild with high and reproducible yields and is selective for addition of β‐nitrostyrenes when compared with other electrophiles. The results obtained from the optimized microwave method consistently provided improved yields in a shorter time compared with those of the conventional heating synthetic route.