Synthesis of 1,2-Dihydroquinazolines via Rearrangement of Indazolium Salts

The Journal of Organic Chemistry
Qian ChenZhonglin Chen

Abstract

A convenient synthesis of 1,2-dihydroquinazolines via rearrangement of indazolium salts was described. A mechanistic study using isotope labeling experiment revealed that the rearrangement passes through cleavage of N-N bond/ring opening after basic deprotonation of 2-benzyl in indazolium salts to yield intermediate E, which proceeds in an intramolecular N-nucleophilic addition to form the observed product. Computational analyses imply that the pathway of the rearrangement is determined by the energy barriers of the ring-closing process and the stability of the product.

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