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Highly regioselective photodimerization of 1,4-dihydropyridines: An efficient synthesis of novel 3,6-diazatetraasteranes

Author:
Tan, Hong-Bo, Zhao, Zhi-Chang, Ma, Zong-Shan, Yan, Hong
Source:
Tetrahedron 2017
ISSN:
0040-4020
Subject:
chemical reactions, chemical structure, organic compounds, regioselectivity
Abstract:
Conventional photocycloaddition of 1,4-dihydropyridines does not afford novel head-to-head 3,6-diazatetraasteranes. Herein, we describe a highly regioselective method to synthesize 3,6-diazatetraasteranes via an intramolecular photodimerization of 1,4-dihydropyridines. First, the 1,4-dihydropyridines were tethered by phthaloyl to direct a proximate parallel arrangement in head-to-head orientation by the rotation of C-C single bonds in solution. An intramolecular [2 + 2] photocycloaddition proceeded subsequently to give desired 3,6-diazatetraasteranes in high yield (92–97%) and excellent regioselectivity. Furthermore, two different 1,4-dihydropyridines can also be regiocontrolled by this strategy and produce polysubstituted 3,6-diazatetraasteranes via a cross-photodimerization in a concise and efficient way. In addition, this approach can provide direct access to other polysubstituted polyhedron scaffolds from 1,4-dihydropyridine analogues.
Agid:
5837356