TRIFLUOROACETIC ACID MEDIATED NUCLEOPHILIC SUBSTITUTION / SMILES REARRANGEMENT CASCADE REACTION: AN ALTERNATIVE APPROACH TO CONSTRUCTING PYRROLE-FUSED DIHYDROPTERIDINES

Authors

  • Tong Zhu The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun, Jilin 130021
  • Jinbao Xiang The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun, Jilin 130021

DOI:

https://doi.org/10.1007/3299

Keywords:

dihydrodiazepines, pyrimidines, pyrrolo[1, 2-f]pteridines, cascade reactions, nucleophilic substitution, Smiles rearrangement

Abstract

A trifluoroacetic acid mediated cascade reaction involving nucleophilic substitution and Smiles rearrangement is described. The reaction of hydroxydihydrodiazepines with primary amines led to amino-substituted dihydrodiazepines, which readily underwent Smiles rearrangement to give pyrrolo[1,2-f]pteridine derivatives.

 

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Published

2016-11-04

Issue

Vol. 52 No. 10 (2016)

Section

Original Papers