443-86-7Relevant articles and documents
Practical synthesis of a benzophenone-based NNRT inhibitor of HIV-1
Wang, Xiao-Jun,Zhang, Li,Sun, Xiufeng,Lee, Heewon,Krishnamurthy, Dhileepkumar,O'Meara, Jeff A.,Landry, Serge,Yoakim, Christiane,Simoneau, Bruno,Yee, Nathan K.,Senanayake, Chris H.
scheme or table, p. 561 - 566 (2012/07/03)
A convergent synthesis of NNRTI 1 is described. The key step involves a direct coupling of acid chloride 4 with Grignard reagent 11 in the presence of bis[2-(N,N-dimethylamino)ethyl] ether that moderates the reactivity of the Grignard reagent to give benzophenone 7. An efficient 2-step process for the preparation of 2-fluoro-3-methyl-4-aminobenzoic acid (3) is also described.
Intramolecular Selectivity of the Alkylation of Substituted Anilines by Gaseous Cations
Attina, Marina,Cacace, Fulvio,de Petris, Giulia
, p. 1556 - 1561 (2007/10/02)
The intramolecular selectivity of the electrophilic reactions of Et(1+), i-Pr(1+), and Me2F(1+) cations with substituted anilines, including m-toluidine, m-anisidine, and m- and p-fluoroaniline, has been investigated in the dilute gas state at pressures ranging from 100 to 720 torr by a radiolytic technique, complemented by chemical ionization mass spectrometry.The results indicate an appreciable kinetic bias for the nitrogen atom, leading to predominant N-methylation by Me2F(1+).The reactivity of the carbenium ions is complicated by the simultaneous occurrence of proton transfer, in particular to the NH2 group, which increases the relative extent of ring alkylation.The positional selectivity is characterized, aside from the usual orienting effects of the substituents, by the enchanced reactivity of the ring positions ortho to an n-type substituent, irrespective of its activating or deactivating properties.The effect is traced to the preliminary formation of an electrostatic adduct between the aniline and the gaseous electrophile.
The synthesis of ortho-substituted 2-diethylaminoethyl benzoates as potential local anaesthetics.
THOMAS,CANTY
, p. 587 - 596 (2007/10/05)
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