Issue 28, 2023

Pd-catalyzed oxidative amination of 2-alkenylquinazolin-4(3H)-ones: synthesis of methylene and vinyl derivatives of pyrrolo(pyrido)[2,1-b]quinazolinones

Abstract

When treated with the catalytic system Pd(OAc)2/PPh3/Cs2CO3/benzoquinone in dioxane or Pd(PPh3)2Cl2/t-BuONa/Cs2CO3/benzoquinone in toluene, 2-butenylquinazolin-4(3H)-ones undergo intramolecular aza-Wacker cyclization to give methylene-substituted pyrrolo(pyrido)[2,1-b]quinazolinones. The latter catalytic system is also efficient in the reaction of pentenyl(hexenyl)quinazolin-4(3H)-ones but, in these cases, the aminopalladation of C–H multiple bonds significantly competed with allylic C(sp3)–H bond activation which leads to hitherto unknown vinyl-substituted pyrrolo(pyrido)[2,1-b]quinazolinones.

Graphical abstract: Pd-catalyzed oxidative amination of 2-alkenylquinazolin-4(3H)-ones: synthesis of methylene and vinyl derivatives of pyrrolo(pyrido)[2,1-b]quinazolinones

Supplementary files

Article information

Article type
Paper
Submitted
26 May 2023
Accepted
27 Jun 2023
First published
27 Jun 2023

Org. Biomol. Chem., 2023,21, 5866-5872

Pd-catalyzed oxidative amination of 2-alkenylquinazolin-4(3H)-ones: synthesis of methylene and vinyl derivatives of pyrrolo(pyrido)[2,1-b]quinazolinones

A. I. Vaskevych, N. O. Savinchuk, R. I. Vaskevych, S. V. Shishkina and M. V. Vovk, Org. Biomol. Chem., 2023, 21, 5866 DOI: 10.1039/D3OB00834G

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