129205-95-4Relevant academic research and scientific papers
CARBON DIOXIDE: A REAGENT FOR THE SIMULTANEOUS PROTECTION OF NUCLEOPHILIC CENTERS AND THE ACTIVATION OF ALTERNATIVE LOCATIONS TO ELECTROPHILIC ATTACK. 16. A NOVEL SYNTHETIC METHOD FOR THE SIDE-CHAIN FUNCTIONALIZATION OF N-METHYL-o-TOLUIDINE AND FOR THE PREPARATION OF 2-SUBSTITUTED...
Katritzky, Alan R.,Fan, Wei-Qiang,Akutagawa, Kunihiko,Wang, Jin
, p. 407 - 414 (2007/10/02)
N-Methyl-o-toluidine is readily converted into a range of side-chain functionalized derivatives in a one-pot sequence, using carbon dioxide for N-protection.The intermediate lithium carbamate is further lithiated by butyllithium at the side-chain methyl group, and then reacted with an electrophile; the product undergoes acid-catalyzed decarboxylation during work-up. 2-Substituted N-methylindoles are produced when carboxylate esters are used as electrophiles.The yields are good, and no ring-substituted products are detected.
