Effect of tetramethylethlylenediamine on the metalation of N-methyl and N-phenylbenzylamine with n-butyllithium. Deuteration and electrophilic condensations of intermediate lithioamines. Cyclodehydrations to give N-substituted isoindolines was written by Ludt, Robert E.;Hauser, Charles R.. And the article was included in Journal of Organic Chemistry in 1971.Application of 5388-42-1 This article mentions the following:
PhCH2NHMe underwent dimetalation with BuLi-Me2NCH2CH2NMe2 (TMEDA) predominantly at the N and the o-benzyl positions as evidenced by deuteration studies. The intermediate o-LiC6H4CH2NMeLi was condensed with BzPh, BzH, cyclohexanone, BzMe, and BzEt. The resulting o-carbinolamines from the BzPh and BzH condensations underwent acid-catalyzed cyclodehydration to form N-methylisoindoline derivatives, while the ortho codensation products from the latter 3 ketones underwent acid-catalyzed linear dehydration reactions, rather than cyclodehydration to form isoindolines. N-Phenylbenzylamine was similarly dimetalated at the N and o-benzyl positions with TMEDA activated BuLi. o-Carbonyl addition reactions of the dilithio amine intermediate with CO2, BzPh, BzH, and 9-fluorenone resulted in an acid and o-carbinolamines, which were readily cyclodehydrated to N-phenylphthalimidine and N-phenylisoindoline derivatives In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application of 5388-42-1).
2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Application of 5388-42-1
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles