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Article Abstract
The present work documents electrophilic substitution of azaarenes, mainly isoquinolines, with hypervalent iodine diazo reagents (HIDR) followed by formal [3+2]-dipolar cycloaddition in a tandem fashion. Other azaarenes pyridines and phenanthridines too could be successfully used in the reaction. The methodology capitalizes on the umpolung nature of α-aryliodonio diazo compounds for installing a nucleophile, azaarene, at their α-position. Subsequent ylide formation and intramolecular 1,5-cyclization furnished 4,3-fused 1,2,4-triazolyl-azaarenes in good yields. The reaction is notable for its mild conditions, operational simplicity and fairly general scope.
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