909390-66-5Relevant articles and documents
Synthesis and pharmacological properties of 5-alkyl substituted nicotine analogs
Wang, Jing,Li, Xi,Yuan, Qianjia,Ren, Jiangmeng,Huang, Jin,Zeng, Bubing
, p. 2813 - 2818 (2012)
This paper describes a concise and practical route to enantiomerically enriched 5-alkyl substituted nicotine analogs. The Vilsmeier reaction was used to construct the nicotinaldehydes ring followed by the introduction of the chiral homoallylic alcohol by organic boron reagent and the cyclization of the pyrrolidine ring through the reduction of a chiral azide. 17 analogs have been synthesized and their corresponding biological activities were tested, in which compounds 10d and 10g exhibit excellent IC50 values against RD and SY-SY5Y. Copyright
Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction
Gangadasu,Narender,Bharath Kumar,Ravinder,Ananda Rao,Ramesh,China Raju,Jayathirtha Rao
, p. 8398 - 8403 (2007/10/03)
Eleven enamides were prepared by adopting different procedures. The various enamides prepared were subjected to Vilsmeier reaction using (i) POCl3/DMF; (ii) diphosgene/DMF; (iii) triphosgene/DMF leading to the formation of various multisubstituted chloronicotinaldehydes. Studies carried out indicate that Vilsmeier reagent concentration and the replacement of POCl3 by diphosgene or triphosgene, provides excellent selectivity and higher yields. Under modified reaction conditions one can get only chloronicotinaldehydes and not the chloropyridines as products. The various advantages in using diphosgene and triphosgene are illustrated. The mechanism of formation of chloronicotinaldehyde was discussed.
