39601-63-3

Upstream product

• 49604-63-9 2-((4-Methoxyphenyl)amino)-N-methylbenzamide 

Downstream Products

• 39601-82-6 [1-(4-methoxy-phenyl)-1,2-dihydro-benzo[d][1,3]thiazin-4-ylidene]-methyl-amine 
• 39601-82-6 C₁₆H₁₆N₂OS 

Relevant academic research and scientific papers

Organic Synthesis with N-Heterocyclic Carbenes of Indazole: Synthesis of Benzo(thio)imidates, Benzo[d][1,3]thiazines and Quinazoline-4-thiones

The N-heterocyclic carbenes of indazole, generated by deprotonation of indazolium salts, proved to be versatile starting materials for organic synthesis. They undergo ring-opening reactions to generate ketenimines which readily add thiols thus affording what are, to the best of our knowledge, the first examples of 2-anilinobenzothioimidates. Water converts the ring-opened intermediates into functionalized 2-anilinobenzamides which can be thionated with Lawesson's reagent and subsequently cyclized with formaldehyde and propionaldehyde, respectively, to give benzo[d][1,3]thiazines and quinazoline-4-thiones. The outcome of the cyclization depends upon the thiobenzamide substitution pattern.