Acid/Base-Steered Cascade Cyclization: An Efficient One-Pot Access to Diverse Isobenzofuranone and Isoindolobenzoxazinone Derivatives

Autor:	Ran Shi, Xiangmin Wang, Xuesi Zhang, Sen Chen, Zu-Li Wang, Huijing Qi, Xin-Ming Xu
Jazyk:	angličtina
Rok vydání:	2023
Předmět:	isoindolobenzoxazinones isobenzofuranones isatoic anhydrides cascade cyclization Organic chemistry QD241-441
Zdroj:	Molecules, Vol 28, Iss 3, p 1443 (2023)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules28031443
Popis:	We herein report the acid/base-steered two distinct reaction pathways of 2-acylbenzoic acids with isatoic anhydrides. In the presence of Na2CO3, the cascade process consists of the cyclization of 2-acetylbenzoic acid and nucleophilic ring-opening reaction of isatoic anhydride to furnish isobenzofuranone derivatives with high efficiency. However, p-toluenesulfonic acid can promote the product isobenzofuranones to undergo sequential intramolecular rearrangment, nucleophilic addition and cyclization reaction to produce diverse isoindolobenzoxazinones in good yields. The synthetic utility of this method was further demonstrated by the gram-scale preparation of the desired products and the facile transformations of the resulting products.
Databáze:	Directory of Open Access Journals
Externí odkaz:	https://doaj.org/article/18988d170a36415d871309f1bffdf74b Zobrazit plný text záznamu View record in DOAJ Plný text ve formátu PDF Plný text ve formátu HTML
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