Synthesis of indole-cycloalkyl[ b]pyridine hybrids via a four-component six-step tandem process

Muthumani Muthu; Rakkappan Vishnu Priya; Abdulrahman I Almansour; Raju Suresh Kumar; Raju Ranjith Kumar

doi:10.3762/bjoc.14.269

Synthesis of indole-cycloalkyl[ b]pyridine hybrids via a four-component six-step tandem process

Beilstein J Org Chem. 2018 Nov 22:14:2907-2915. doi: 10.3762/bjoc.14.269. eCollection 2018.

Authors

Muthumani Muthu¹, Rakkappan Vishnu Priya², Abdulrahman I Almansour³, Raju Suresh Kumar³, Raju Ranjith Kumar¹

Affiliations

¹ Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamil Nadu, India.
² Department of Physics, Madura College, Madurai 625011, Tamil Nadu, India.
³ Department of Chemistry, College of Science, King Saud University, Riyadh 11451, Saudi Arabia.

Abstract

The one-pot four-component reaction of 3-(1H-indol-3-yl)-3-oxopropanenitriles, aromatic aldehydes, cycloalkanones and ammonium acetate occurred via a six-step tandem Knoevenagel condensation-nucleophilic addition to carbonyl-Michael addition-N-cyclization-elimination-air oxidation sequence to afford structurally intriguing indole-cycloalkyl[b]pyridine-3-carbonitrile hybrid heterocycles in excellent yields.

Keywords: 3-(1H-indol-3-yl)-3-oxopropanenitrile; cycloalkyl[b]pyridine-3-carbonitrile; cyclododecanone; tandem reaction.