198020-49-4

Upstream product

• 36684-49-8 2-iodo-N-(4-methoxyphenyl)benzamide 
• 1066-54-2 trimethylsilylacetylene 
• 88-67-5 2-Iodobenzoic acid 
• 609-67-6 2-Iodobenzoyl chloride 
• 118-92-3 anthranilic acid 

Downstream Products

• 69643-85-2 2-(4-Methoxy-phenyl)-3-[2-oxo-2-phenyl-eth-(Z)-ylidene]-2,3-dihydro-isoindol-1-one 
• 251653-89-1 (E)-N-p-methoxyphenyl-3-[(2'-oxo-2'-p-methylphenyl)ethylidene]isoindolin-1-one 
• 218787-68-9 2,3-dihydro-3-methylene-2-(4'-methoxyphenyl)-1H-isoindolone 

Relevant academic research and scientific papers

Product selectivity control in the heteroannulation of o-(1-Alkynyl)benzamides

The selective synthesis of (Z)- or (E)-3-aryl/vinyl/alkylidene-isoindolones, and 2-benzopyran derivatives from o-(1-alkynyl)benzamides by means of a suitable choice of bases or silver catalysis is described.

Palladium-catalysed heteroannulation with terminal alkynes: A highly regio- and stereoselective synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1- ones

A highly regio- and stereoselective method for the synthesis of (Z)-3- aryl(alkyl)idene isoindolin-1-ones through palladium-copper catalysis is described. 2-Iodobenzamide 1 and its substituted derivatives 2-10 were reacted with terminal alkynes 11-19 in the presence of (PPh3)2PdCl2, CuI, and Et3N in DMF mostly at 80°C for 16 h to yield the 2-alkynyl substituted benzamides 20-38, 40-45, 77 which could then be cyclised with NaOEt in EtOH to the 3-aryl(alkyl)idene isoindolin-1-ones 46-49, 51, 53-55, 57, 59-71, 73 and 75. In certain cases, the isoindolin-1-ones 50, 52, 56 and 58 could be directly obtained by the palladium-catalysed reactions. (C) 2000 Elsevier Science Ltd.

Heteroannulation through combined palladium catalysed and Friedel-Crafts reactions strategy: Synthesis of 3-alkylidene isoindolin-1-ones

The palladium-catalysed reactions of 2-iodobenzamides 1-5 with trimethylsilyl acetylene 6 led to 2-(2-trimethylsilyl)ethynyl benzamides 7-11 in excellent yields. The 2-(2-trimethylsilyl)ethynyl benzamides 7-11 underwent Friedel-Crafts reactions with acid

An expeditious synthesis of Z-3-alkylidene isoindolinones via combined palladium catalysed and Friedel-Crafts reactions

N-Aryl(or, alkyl)-2-iodobenzamides underwent palladium-catalysed reaction with (trimethylsilyl)acetylene to form N-substituted-2-(trimethylsilyl)ethynyl benzamides, which on further Friedel-Crafts acylation and cyclisation yielded Z-3-alkylidene isoindolin-1-ones in a completely regio- and stereoselective manner.