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A new tactic for the synthesis and selective functionalization of [1,2,4]triazolo[4,3-a]pyrazines has been developed using an oxidative cyclization as key step. Furthermore, novel strategies for introducing diverse substituents in all positions of the heterocycle were identified.

A one-pot, two-step reaction for the synthesis of benzo[4,5]thiazolo[2,3- c ][1,2,4]triazoles and related heterocycles under mild conditions was herein developed. The key step of this transformation is an oxidative cyclization employing PhI(OAc) 2 as reagent. Scope and limitations (group functionality tolerance and sterics) were studied showing the robustness of the present methodology which can be used as potential access to new fused heterocycle libraries.

A new convenient three-step synthesis of the privileged CNS scaffold1,2,3,4,10,10a-hexahydropyrazino[1,2- A]indoleshas been developed. The method makes use of an intramolecular carbene-mediatedC-H insertion in phenylpiperazine-derived tosyl-hydrazonesmade from 2-fluorobenzaldehydes. Notably, the piperazine can bereplaced with other cyclic nitrogen bases and the methodology issuccessfully extended to pyrrolidine, piperidine, azepane, morpholine,and homopiperazine.

A versatile procedure for the synthesis of optically pure 1-amino-3-aryl indanes is presented, exemplified by the synthesis of the triple uptake inhibitor (+)-indatraline (1).