A convenient synthesis of flindersine, atanine and their analogues

An efficient synthesis of fluorine-containing substituted spiro[piperidine-4,4′-pyrano[3,2-c]quinoline]-3′-carbonitrile by nonconventional methods

“…For synthesis of novel spiro derivatives, at first we attempted to obtain unsaturated nitrile (Scheme 1) by the condensation of piperidin-4-one (2a) and malononitrile (3), but the resulting compound is unstable and dimerized at room temperature to form spiropiperidinoisoquinoline (4a) [19,20] within 2-3 min after mixing the reactants (chromatographic monitoring).…”

“…Pyrano quinoline moiety is also present in many naturally occurring bioactive alkaloids such as flindersine, oricine and vesprisine [3], simulenoline [4,5], huajiaosimuline [6] and zanthodioline.…”

Bleaching earth clay (pH 12.5)/PEG-400: an efficient recyclable catalytic system for synthesis of 5,6,7,8-tetrahydroquinoline-3-carbonitrile derivatives

“…The tetrahydroquinoline framework is considered to be one of the privileged structures in the area of drug discovery, as compounds containing this scaffold display a wide range of biological and pharmaceutical activities [4][5][6][7][8][9][10][11][12], including anti-human immunodeficiency virus (HIV) [13,14], anticancer [15,16], and antimalarial action [17], cholesteryl ester transfer protein inhibition [18], antidiabetic [19] and antifungal activity [20], C 5a receptor antagonism [21], RET tyrosine kinase inhibition [22], etc.…”

A mild and efficient synthesis of chiral tetrahydroquinolino pyranose derivatives catalyzed by lanthanum(iii) nitrate hexahydrate

“…Therefore, many synthetic methods have been developed for these classes of compounds. Most of the methods employed the hetero Diels-Alder method using different Lewis acids such as BF 3 ·OEt 2 [9], ZnCl 2 [10], BiCl 3 [11], and InCl 3 [12,13] and Brönsted acids such as HBF 4 , CF 3 COOH, TsOH [14], and also mineral acids [15] to produce 2,3-tetrahydroquinolinated pyranose derivatives. Recently, Yadav et al reported the synthesis of 2,4-tetrahydroquinolinated pyranose derivatives using InBr 3 , Bi(OTf) 3 , and CeCl 3 /NaI [16][17][18].…”