2H-Azirine-2-carbonyl Azides: Preparation and Use as N-Heterocyclic Building Blocks

Результат исследований: Научные публикации в периодических изданияхстатья

1 Цитирования (Scopus)

Аннотация

2H-Azirine-2-carbonyl azides, new reactive heterocyclic building blocks, were synthesized in high yield by the reaction of sodium azide with 2H-azirine-2-carbonyl chlorides, generated by the Fe(II)-catalyzed isomerization of 5-chloroisoxazoles. 2-(Azidocarbonyl)-1H-pyrroles, prepared by the Ni(II)-catalyzed reaction of 2-(azidocarbonyl)-2H-azirines with 1,3-diketones, easily undergo the Curtius rearrangement in boiling tBuOH to give Boc-protected α-aminopyrroles in high yield. Heating of 2-(azidocarbonyl)-1H-pyrroles for a short time in inert solvents leads to the high-yield formation of benzo- A nd hetero-fused 1H-pyrrolo[2,3-b]pyridin-6(7H)-ones, which are formed via a 6πelectrocyclization involving the vicinal aryl or hetaryl substituent and the Nâ•C bond of isocyanate, generated by the Curtius rearrangement of the azidocarbonyl group. The Pd-catalyzed cross-coupling reaction of 1-acetyl-2-methyl-3H-pyrrolo[2,3-c]isoquinolin-5-yl triflate, easily prepared from the corresponding pyrroloisoquinolone, leads to variously 5-substituted 3H-pyrrolo[2,3-c]isoquinolines in excellent yields.

Язык оригиналаанглийский
Страницы (с-по)4182-4194
Число страниц13
ЖурналJournal of Organic Chemistry
Том85
Номер выпуска6
DOI
СостояниеОпубликовано - 20 мар 2020

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Предметные области Scopus

  • Органическая химия

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