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Updated: May 5, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Organocatalytic [4+2] Benzannulation Between 1,4-Dithiane-Based Enal and Nitroolefins to Access 2-Nitrobiaryls
Imtiyaz Ahmad Shah1, Yadav Kacharu Nagare1, Krishnan Rangan2
1Department of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, Rajasthan, India.
Abstract:
A simple method for constructing unsymmetrical 2-nitrobiaryls has been developed between substituted 1,4-dithiine-2-carbaldehyde and nitroolefins under metal-free conditions. To gain the advantage of the HOMO-raising effect of temporary substitutions on in situ generated dienamine intermediate, the present protocol established [4+2] benzannulation of 1,4-dithiane-tethered enals with nitroolefin. Further, easy unmasking of 1,4-dithiine units results in a benzannulation product like that of unsubstituted enals, which are difficult to access. Several 2-nitrobiaryls have been accessed with moderate to good yields and with promising synthetic applications.
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