Citation: Pu Hua Wu, Qing Qing Meng, Hu Chen Zhou. Synthesis of a novel pyrrolo-benzoxaborole scaffold and its derivatization via Friedel-Crafts reaction catalyzed by anhydrous stannic chloride[J]. Chinese Chemical Letters, ;2011, 22(12): 1411-1414. doi: 10.1016/j.cclet.2011.06.005 shu

Synthesis of a novel pyrrolo-benzoxaborole scaffold and its derivatization via Friedel-Crafts reaction catalyzed by anhydrous stannic chloride

School of Pharmacy, Shanghai Jiaotong University, Shanghai 200240, China

Received Date: 28 April 2011

Fund Project: We thank National Science Foundation of China (No.20702031), Ministry of Science and Technology of China (No.2009CB918404), E-Institutes of Shanghai Universities (EISU) Chemical Biology Division, and National Comprehensive Technology Platforms for Innovative Drug R&D (No.2009ZX09301-007) for financial support of this work.We also thank Instrumental Analysis Center of SJTU for providing the NMR service.

A novel pyrrolo-benzoxaborole, 6-(pyrrol-l-yl)-l, 3-dihydro-l-hydroxy-2, 1-benzoxaborole, was synthesized with 27% overall yield over six steps from 2-bromo-1-methyl-4-nitrobenzene as starting material. Its derivatization was achieved via Friedel-Crafts reaction catalyzed by anhydrous stannic chloride with various acyl chlorides giving 3-acyl-1-phenylpyrroles as the main products.
- Benzoxaborole,
- Friedel-Crafts reaction,
- Stannic chloride,
- 3-Acyl-1-arylpyrrole
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