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

Tong Zhu, Jinbao Xiang
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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.

 


Keywords


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

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