Synthesis of Polysubstituted Benzo[ b][1,5]naphthyridine via Mn(III)-Mediated Domino Cascade Reactions of Cyclopropanols and 2-(2-Isocyanophenyl)acetonitriles

Shiqiang Mu; Qingqing Xuan; Ying Luo; Yu Guo; Jian Xu; Qiuling Song

doi:10.1021/acs.orglett.4c04097

Synthesis of Polysubstituted Benzo[ b][1,5]naphthyridine via Mn(III)-Mediated Domino Cascade Reactions of Cyclopropanols and 2-(2-Isocyanophenyl)acetonitriles

Org Lett. 2025 Jan 2. doi: 10.1021/acs.orglett.4c04097. Online ahead of print.

Authors

Shiqiang Mu¹, Qingqing Xuan¹, Ying Luo¹, Yu Guo¹, Jian Xu¹, Qiuling Song^{1

2

3

4}

Affiliations

¹ Institute of Next Generation Matter Transformation, College of Material Sciences Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian 361021, China.
² Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou 350108, China.
³ State Key Laboratory of Organometallic Chemistry and Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
⁴ School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

PMID: 39745004
DOI: 10.1021/acs.orglett.4c04097

Abstract

Domino cascade reactions, which can construct multiple bonds in one pot, are efficient methods to synthesize N-heterocycles and other useful skeletons. Herein, we report an expedient synthesis of polysubstituted benzo[b][1,5]naphthyridine via Mn(III)-mediated C-C bond cleavage of cyclopropanols. These reactions were initiated by addition of β-carbonyl radicals, generated from cyclopropyl alcohols in the presence of Mn(III), to 2-(2-isocyanophenyl)acetonitriles to give quinolin-3-amines, which went through intramolecular cyclizations and dehydrogenation to give the final products.