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

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

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

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

Afiliación

Vaskevych AI; Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Academician Kukhar str., 5, Kyiv 02660, Ukraine. a.yu.vaskevich@gmail.com.
Savinchuk NO; Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Academician Kukhar str., 5, Kyiv 02660, Ukraine. a.yu.vaskevich@gmail.com.
Vaskevych RI; Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Academician Kukhar str., 5, Kyiv 02660, Ukraine. a.yu.vaskevich@gmail.com.
Shishkina SV; Enamine Ltd, Chervonotkatska str. 78, Kyiv 02094, Ukraine.
Vovk MV; State Scientific Institution "Institute for Single Crystals", National Academy of Sciences of Ukraine, 61072, prosp. Nauky, 60, Kharkiv, Ukraine.

Org Biomol Chem ; 21(28): 5866-5872, 2023 Jul 19.

Article en En | MEDLINE | ID: mdl-37404065

RESUMEN

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.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2023 Tipo del documento: Article País de afiliación: Ucrania Pais de publicación: Reino Unido

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