Base-catalyzed rearrangement of N-(aryloxy) pyridinium salts. Effect of a 3-substituent in the pyridine ring upon orientation. Synthesis of novel tricyclic rings

RA Abramovitch, MN Inbasekaran, S Kato…

Index: Abramovitch, Rudolph A.; Inbasekaran, Muthiah N.; Kato, Shozo; Radzikowska, Teresa A.; Tomasik, Piotr Journal of Organic Chemistry, 1983 , vol. 48, # 5 p. 690 - 695

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Citation Number: 13

Abstract

The orientation in the base-catalyzed rearrangement of 3-substituted N-(ary1oxy) pyridinium ktrafluoroboraks (5) to 2-or 6-(2-hydroxyaryl) pyridines has been studied. A 3-methyl group directs exclusively to the 6-position while inductively electron-withdrawing substituents (Cl, Br, I, OMe, C02Me, COMe) direct mainly, if not exclusively, to C-2. The phenols derived from 3-C02Me derivatives cyclize spontaneously to the substituted pyrido [3, 2-dicoumarins (8) ...