Aryne [3 + 2] cycloaddition with N-sulfonylpyridinium imides and in situ generated N-sulfonylisoquinolinium imides: a potential route to pyrido[1,2-b]indazoles and indazolo[3,2-a]isoquinolines was written by Zhao, Jingjing;Li, Pan;Wu, Chunrui;Chen, Hongli;Ai, Wenying;Sun, Renhong;Ren, Hailong;Larock, Richard C.;Shi, Feng. And the article was included in Organic & Biomolecular Chemistry in 2012.Reference of 1186603-47-3 The following contents are mentioned in the article:
The aryne [3 + 2] cycloaddition process with pyridinium imides breaks the aromaticity of the pyridine ring. By equipping the imide nitrogen with a sulfonyl group, the intermediate readily eliminates a sulfinate anion to restore the aromaticity, leading to the formation of pyrido[1,2-b]indazoles. E.g., [3 + 2] cycloaddition of the aryne formed from 3-methoxy-2-trimethylsilylphenyl triflate with N-tosylpyridinium imide gave 77% pyrido[1,2-b]indazole (I). The scope and limitation of this reaction are discussed. As an extension of this chem., N-tosylisoquinolinium imides, generated in situ from N’-(2-alkynylbenzylidene)tosylhydrazides via an AgOTf-catalyzed 6-endo-dig electrophilic cyclization, readily undergo aryne [3 + 2] cycloaddition to afford indazolo[3,2-a]isoquinolines in the same pot, offering a highly efficient route to these potential anticancer agents. This study involved multiple reactions and reactants, such as 5-Chloro-2-(phenylethynyl)benzaldehyde (cas: 1186603-47-3Reference of 1186603-47-3).
5-Chloro-2-(phenylethynyl)benzaldehyde (cas: 1186603-47-3) belongs to organic chlorides. Chlorination modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than water due to the higher atomic weight of chlorine versus hydrogen. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Reference of 1186603-47-3
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics