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.
Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N -propargylanilines with diverse carbon pronucleophiles: Facile access to functionalized tetrahydroquinolines
Li, Guangzhe,Wang, Chengdong,Li, Yueqing,Shao, Kun,Yu, Guo,Wang, Shisheng,Guo, Xiuhan,Zhao, Weijie,Nakamura, Hiroyuki
, p. 7333 - 7336 (2020/07/23)
Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with two types of carbon pronucleophiles (nitromethane as a sp3 carbon pronucleophile and phenylacetylenes as sp carbon pronucleophiles) proceeded to give the 2-substituted tetrahydroquinolines in good yields with 100percent atomic utilization without any additional external oxidants.