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Linear and V‐Shaped Alkynyl‐1,3,5‐triazines
Author(s) -
Gao Peisen,
Wang Zhenhua,
Wang Xiu,
Zhang Weiqiang,
Gao Ziwei
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500948
Subject(s) - chemistry , sonogashira coupling , moiety , bimetallic strip , regioselectivity , intermolecular force , triazine , copper , catalysis , stereochemistry , medicinal chemistry , molecule , crystallography , polymer chemistry , palladium , organic chemistry
A concise route for the synthesis of linear and V‐shaped alkynyl‐1,3,5‐triazines has been developed by starting from 2,4‐dichloro‐1,3,5‐triazine derivatives. The sequential substitution of the 2‐ and 4‐chloro groups by a regioselective Sonogashira coupling reaction afforded symmetric and unsymmetric V‐shaped alkynyl‐1,3,5‐triazines. A modulated copper‐free Pd/1,10‐phenanthroline catalyst system showed good compatibility with the –OCH 3 , –NPh 2 , and p ‐CH 3 OC 6 H 4 – substitutents and furnished the targeted linear alkynyl‐1,3,5‐triazines in good yields. A Pd/Ag bimetallic system afforded the desired symmetric and unsymmetric V‐shaped alkynyl‐1,3,5‐triazines in moderate to good yields. The photophysical properties of the new alkynyl‐1,3,5‐triazine compounds were characterized experimentally. The X‐ray diffraction analysis of 2a confirmed a coplanar position between the phenyl group and the 1,3,5‐triazinal moiety. Intermolecular π–π interactions were observed between two of the TZ units, and the shortest atomic contact distance between the phenyl moieties of two adjacent molecules is 3.655 Å.