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

Alla I Vaskevych; Nataliia O Savinchuk; Ruslan I Vaskevych; Svitlana V Shishkina; Mykhailo V Vovk

doi:10.1039/d3ob00834g

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

Org Biomol Chem. 2023 Jul 19;21(28):5866-5872. doi: 10.1039/d3ob00834g.

Authors

Alla I Vaskevych¹, Nataliia O Savinchuk¹, Ruslan I Vaskevych^{1

2}, Svitlana V Shishkina³, Mykhailo V Vovk¹

Affiliations

¹ Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Academician Kukhar str., 5, Kyiv 02660, Ukraine. a.yu.vaskevich@gmail.com.
² Enamine Ltd, Chervonotkatska str. 78, Kyiv 02094, Ukraine.
³ State Scientific Institution "Institute for Single Crystals", National Academy of Sciences of Ukraine, 61072, prosp. Nauky, 60, Kharkiv, Ukraine.

PMID: 37404065
DOI: 10.1039/d3ob00834g

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.