442-33-1Relevant articles and documents
A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (?)-cuspareine
Madhubabu,Shankar,Krishna,Kumar, Y. Satish,Chiranjeevi,Muralikrishna, Ch,Mohan, H. Rama,More, Satish S.,Rao, M.V. Basaveswara,Akula, Raghunadh
, p. 1803 - 1807 (2017)
A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (?)-cuspareine via enantiospecific construction of the (R)-benzyl 2-formyl-3,4-dihydroquinoline-1(2H)-carboxylate. We have achieved an efficient enantiospe
Enantioselective Copper-Catalyzed Quinoline Alkynylation
Pappoppula, Mukesh,Cardoso, Flavio S. P.,Garrett, B. Owen,Aponick, Aaron
, p. 15202 - 15206 (2015)
A highly enantioselective copper-catalyzed alkynylation of quinolinium salts is reported. The reaction employs StackPhos, a newly developed imidazole-based chiral biaryl P,N ligand, and copper bromide to effect a three-component reaction between a quinoline, a terminal alkyne, and ethyl chloroformate. Under the reaction conditions, the desired products are delivered in high yields with ee values of up to 98 %. The transformation tolerates a wide range of functional groups with respect to both the alkyne and the quinoline starting materials and the products are easily transformed into useful synthons. Efficient, enantioselective syntheses of the tetrahydroquinoline alkaloids (+)-galipinine, (+)-angustureine, and (-)-cuspareine are reported.
Enantioselective synthesis of tetrahydroquinoline alkaloids (-)-angustureine and (-)-cuspareine from chiral tert-butanesulfinyl imines
Sirvent, Juan A.,Foubelo, Francisco,Yus, Miguel
, p. 1163 - 1174 (2014)
The addition of a Grignard reagent to both enantiomeric N-tert-butanesulfinyl imines derived from 3-(2-bromophenyl)propanal 8 proceeded with high diastereoselectivity. The resulting sulfinamides 9 and 12 were easily transformed into tetrahydroquinoline alkaloids (-)-angustureine (4) and (-)-cuspareine (5) after three steps: N-desulfinylation, intramolecular N-arylation and N-methylation.
Manganese catalyzed C-alkylation of methylN-heteroarenes with primary alcohols
Jana, Akash,Kumar, Amol,Maji, Biplab
, p. 3026 - 3029 (2021/03/29)
C-Alkylations of nine different classes of methyl-substitutedN-heteroarenes, including quinolines, quinoxalines, benzimidazoles, benzoxazoles, pyrazines, pyrimidines, pyridazines, pyridines, and triazines are disclosed. A bench stable earth-abundant Mn(i)-complex catalyzed the chemoselective hydrogen-transfer reaction utilizing a diverse range of primary alcohols as the non-fossil fuel-derived carbon source. The diversifiedN-heteroarenes (41 examples) were isolated in high yields and selectivities. Water is produced as the sole byproduct, making the protocol environmentally benign.
Boric acid catalyzed chemoselective reduction of quinolines
Adhikari, Priyanka,Bhattacharyya, Dipanjan,Das, Animesh,Konwar, Monuranjan,Nandi, Sekhar,Sarmah, Bikash Kumar
supporting information, p. 1214 - 1220 (2020/02/22)
Boric acid promoted transfer hydrogenation of substituted quinolines to synthetically versatile 1,2,3,4-tetrahydroquinolines (1,2,3,4-THQs) was described under mild reaction conditions using a Hantzsch ester as a mild organic hydrogen source. This methodology is practical and efficient, where isolated yields are excellent and reducible functional groups are well tolerated in the N-heteroarene moiety. The reaction parameters and tentative mechanistic pathways are demonstrated by various control experiments and NMR studies. The present work can also be scaled up to obtain gram quantities and the utility of the developed process is illustrated by the transformation of 1,2,3,4-THQs into a series of biologically important molecules including the antiarrhythmic drug nicainoprol.
