Synthesis of [1, 2, 3]‐Triazolo[5, 1‐a]‐isoquinolines through TBAF‐Promoted Cascade Reactions. Issue 1 (14th December 2020)

• Record Type: Journal Article
• Authors: Duan, Shengguo; Chen, Yidian; Meng, Hui; Shan, Lihong; Xu, Ze‐Feng; Li, Chuan‐Ying
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 1(2021)
• Page Start: 224
• Page End: 232
• Publication Date: 2020-12-14
• Subjects: triazolo[5, 1-a]isoquinoline -- TBAF -- detosylation -- cyclization -- isoquinoline; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202000618
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A tetrabutylammonium fluoride (TBAF)‐promoted detosylation cyclization cascade was developed for the synthesis of [1, 2, 3]‐triazolo[5, 1‐ a ]‐isoquinolines. Most of the products were obtained in excellent yields under mild conditions. Valuable halogen‐substituted [1, 2, 3]‐triazolo[5, 1‐ a ]‐isoquinolines could also be synthesized with a slight modification of the reaction conditions. Functionalized isoquinolines were obtained smoothly by denitrogenative reactions. The control experiments showed that this transformation was facilitated by TBAF and the water contained in the commercially obtained reagent. Deuterium labeling products could also be obtained easily in high yield. Abstract : [1, 2, 3]‐Triazolo[5, 1‐ a ]‐isoquinolines could be synthesized in excellent yields via a TBAF‐promoted cascade reaction under mild conditions. The halogen could be installed at different positions of [1, 2, 3]‐triazolo[5, 1‐ a ]‐isoquinolines. This transformation was facilitated by TBAF and the water contained in the commercially obtained reagent. Deuterium labeling products could be obtained easily in high yields.