Synthesis of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[ c][2,7]naphthyrin-5(6 H)-one

Shobanbabu Bommagani; Na-Ra Lee; Xuan Zhang; Linda P Dwoskin; Guangrong Zheng

doi:10.1016/j.tetlet.2015.09.156

Synthesis of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[ c][2,7]naphthyrin-5(6 H)-one

Tetrahedron Lett. 2015 Nov 18;56(46):6472-6474. doi: 10.1016/j.tetlet.2015.09.156.

Authors

Shobanbabu Bommagani¹, Na-Ra Lee², Xuan Zhang¹, Linda P Dwoskin², Guangrong Zheng¹

Affiliations

¹ Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.
² Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA.

Abstract

Efficient syntheses of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one are presented. The O-alkylated analogues were synthesized through a reduction-cyclization cascade and a selective O-alkylation reaction; whereas the N-alkylated analogues were obtained through a key Buchwald coupling.

Keywords: 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one; Buchwald coupling; Muscarinic acetylcholine receptors; Reduction-cyclization cascade; Suzuki coupling.

Abstract

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