Ruthenium-Catalyzed Regioselective Alkenylation/Tandem Hydroamidative Cyclization of Unmasked Quinazolinones Using Terminal Alkynes

The Journal of Organic Chemistry
Amol B Viveki, Santosh B Mhaske

Abstract

Ruthenium-catalyzed amide directed Csp2-H activation of the quinazolinone scaffold has been demonstrated, leading to the selective mono- or dialkenylation in moderate to good yields to achieve medicinally important stilbene containing quinazolinones. The terminal alkyne is utilized as a coupling partner, which resulted in the selective trans-alkene formation. Electron-deficient phenylacetylenes facilitate alkenylation followed by tandem hydroamidation of the newly generated trans-double bond to provide novel quinazolinone alkaloids related to the Luotonine class of natural products.

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Citations

Jan 14, 2020·Chemical Communications : Chem Comm·Amol B VivekiSantosh B Mhaske
May 30, 2020·Organic & Biomolecular Chemistry·Prasanjit GhoshSajal Das
Jan 29, 2019·The Journal of Organic Chemistry·Rajendra S RohokaleChepuri V Ramana

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