Acid-catalyzed ring-expansion of 4-(1-hydroxycyclobutyl)-1, 2, 3-triazoles. Issue 4 (17th January 2022)

• Record Type: Journal Article
• Authors: Xu, Mingchuan; Liu, Lei; Wang, Tao; Luo, Han; Hou, Meili; Du, Luan; Xin, Xiaolan; Lu, Qixing; Li, Baosheng
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 4(2022)
• Page Start: 1065
• Page End: 1069
• Publication Date: 2022-01-17
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo01747k
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A direct ring-opening/semipinacol rearrangement reaction catalyzed by the Brønsted acid of 4-(1-hydroxycyclobutyl)-1, 2, 3-triazole is reported, in which the usage of metal catalysts and the reservation of sulfonyl groups are avoided. Abstract : We here report a direct ring-opening/semipinacol rearrangement reaction of 4-(1-hydroxycyclobutyl)-1, 2, 3-triazole, in which N -acyl substituted 1, 2, 3-triazole was generated in situ and would trigger thermodynamically controlled electrocyclization ring-opening to afford a rearrangement precursor ( α -diazo-ol). This strategy avoided the usage of metal catalysts and the reservation of sulfonyl groups on the N 1 -position of 1, 2, 3-triazole. The final cycloenaminone product is highly reactive and could be commonly used as a dinucleophilic acceptor to synthesize structurally diverse fused bicyclic products.