An efficient CuI-L-proline catalyzed one-pot synthesis was developed to generate a collection of skeletally diverse heterocyclic ring systems with sizes ranging from 6 to 9. A salient feature of this design strategy is its modular synthetic utility using an SN2 reaction followed by a microwave assisted CuI-L-proline hetero-arylation, which has granted access to a series of novel heterocyclic frameworks including: benzo[e]pyrrolo[1,2-a][1,4]diazepin, benzo[e]pyrrolo[1,2-a][1,4]diazocin, benzo[e]pyrido[1,2-a][1,4]diazocinones, dibenzo[b,f][1,5]diazoninones, dihydrodibenzo[b,e][1,4]thiazepine, dibenzo[b,e][1,4]thiazocine and benzo[6,7][1,4]diazepino[1,2-a]indole. The synthetic procedures described herein, has allowed rapid entries to a wide range of previously inaccessible and synthetically challenging poly-heterocyclic systems with good overall yields.

Modular cuI-proline catalyzed one-pot route for the rapid access of privileged small and medium ring systems

253rd National Meeting (2017)

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