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

  • J Heterocycl Chem. 2017 May;54(3):2079-2084. doi: 10.1002/jhet.2861.
Pushkar M Kulkarni  1 Ameya Ranade  1 Sumanta Garai  1 Ganesh A Thakur  1
Affiliations
  • 1. Department of Pharmaceutical Sciences, School of Pharmacy, Bouvé College of Health Sciences, Northeastern University, Boston, MA 02115, USA.
Abstract

2-Arylindoles, in general exhibit reduced reactivity towards the conjugate addition to substituted nitrostyrenes, when compared to 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 to Other electrophiles. The results obtained from the optimized microwave method consistently provided improved yields in a shorter time compared to those of the conventional heating synthetic route.

Keywords
2-Arylindole; Cannabinoid receptor; Conjugate addition; Microwave-assisted synthesis; β-Nitrostyrene.
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