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Microwave‐Enhanced Rhodium‐Catalyzed [2+2+2] Cycloaddition Reactions To Afford Highly Functionalized Pyridines and Bipyridines
Author(s) -
Garcia Lídia,
PlaQuintana Anna,
Roglans Anna,
Parella Teodor
Publication year - 2010
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.200901318
Subject(s) - cycloaddition , rhodium , chemistry , catalysis , pyridine , intramolecular force , microwave chemistry , combinatorial chemistry , photochemistry , microwave , organic chemistry , microwave irradiation , physics , quantum mechanics
Abstract Rhodium(I)‐catalyzed [2+2+2] cycloaddition reactions of N ‐tosyl‐, carbon‐, and oxygen‐tethered cyanodiynes in a completely intramolecular fashion have been optimized to afford highly functionalized pyridines by conventional and/or microwave heating. Microwaves have been shown to enhance the process by allowing the reaction to be conducted effectively in short reaction times. The methodology has been extended for the synthesis of bipyridines, either by treating a cyanodiyne with an appended pyridine or by conducting a double [2+2+2] cycloaddition reaction on a dicyanotetrayne scaffold. The choice of the solvent in the microwave heating reaction has been shown to be crucial for the success of the process.