Synthesis of a novel tetracyclic azaindolo[2,1-c][1,4]benzoxazine ring system |
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Authors: | Santosh KurhadeRahul D Kaduskar Bhavesh DaveParimi Atchuta Ramaiah Venkata P PalleDebnath Bhuniya |
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Institution: | a Drug Discovery Facility, Advinus Therapeutics Ltd, Quantum Towers, Plot-9, Rajiv Gandhi Infotech Park, Phase-I, Hinjewadi, Pune 411 057, India b Department of Organic Chemistry, Andhra University, Visakhapatnam 530 003, India |
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Abstract: | Synthesis of a series of novel fused tetracyclic mono- and diazaindolo2,1-c]1,4]benzoxazine heterocyclic compounds 3a-o has been achieved in a two-step one-pot reaction set up starting from commercially available or easily accessible inputs. For example, reaction of di-lithiated (N-Boc)-2-amino-3-methylpyridine Li2-2a with Weinreb amide of 2-(2,4-difluorophenoxy)-2,2-dimethylacetic acid 1a, followed by TFA treatment furnished the tetracyclic compound 3a, which is essentially a fusion of 7-azaindole and 3,4-dihydro1,4]benzoxazine, in 70% isolated yield. A competitive elimination by-product 4a was also observed (24% isolated yield) in this case. Based on our initial results, a structural basis and molecular mechanism have been suggested to explain these two parallel reactions. Consequently, with appropriate structural tuning of 1, formation of the individual products can be controlled. |
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Keywords: | Azaindolo[2 1-c][1 4]benzoxazine Diazaindolo[2 1-c][1 4]benzoxazine (N-Boc)-2-amino-3-methylpyridine 2-(2 4-Difluorophenoxy)-2 2-dimethylacetic acid Weinreb amide |
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