TEMPO-Mediated Synthesis of Indolyl/Imidazo[1,2-a]pyridinyl-Substituted para-Quinone Methides from Butylated Hydroxytoluene

Autor:	Dhananjay S. Nipate, Vikki N. Shinde, Sonam, Anil Kumar, Krishnan Rangan
Rok vydání:	2021
Předmět:	chemistry.chemical_compound Reaction mechanism Chemistry Organic Chemistry Functional group Para-quinone Butylated hydroxytoluene Substrate (chemistry) Medicinal chemistry
Zdroj:	The Journal of Organic Chemistry. 86:17090-17100
ISSN:	1520-6904 0022-3263
Popis:	A series of indolyl or imidazo[1,2-a]pyridinyl-substituted para-quinone methides (p-QMs) is prepared by a metal-free, TEMPO-mediated cross-dehydrogenative coupling of butylated hydroxytoluene (BHT) with indoles or imidazo[1,2-a]pyridines in good to high yields. Broad substrate scope with respect to indoles and imidazo[1,2-a]pyridines, good functional group tolerance, and acid/base-free conditions are advantageous feature of the developed protocol. The method was amenable for scale-up on the gram scale. Based on control experiments, a reaction mechanism is proposed to describe this transformation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::552b980165f2b4228d4c794068afedca https://doi.org/10.1021/acs.joc.1c02202 Zobrazit plný text záznamu