Organic Letters
Organic Letters
5 years ago

Synthesis of Fused Polycyclic 1,4-Benzodiazepines via Metal-Free Cascade [5 + 2]/[2 + 2] Cycloadditions

Synthesis of Fused Polycyclic 1,4-Benzodiazepines via Metal-Free Cascade [5 + 2]/[2 + 2] Cycloadditions
Jiyoun Lee, Nirupam De, Eun Jeong Yoo, Jinhwan Shin, Donguk Ko
A metal-catalyst-free, mild, and efficient synthetic protocol for polycyclic 1,4-benzodiazepines via cascade [5 + 2]/[2 + 2] cycloadditions between pyridinium zwitterions and arynes is reported. Mechanistic experiments revealed that pyridinium zwitterions act as 1,5-dipoles in [5 + 2] cycloadditions with arynes for the construction of 1,4-benzodiazepines, which further undergo [2 + 2] cycloaddition resulting in the one-pot formation of one C–N bond and three C–C bonds.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01137

DOI: 10.1021/acs.orglett.7b01137

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