Bunce, Richard A.; Herron, Derrick M.; Johnson, Lara B.; Kotturi, Sharadsrikar V. published the artcile< Diastereoselective synthesis of substituted tetrahydroquinoline-4-carboxylic esters by a tandem reduction-reductive amination reaction>, Recommanded Product: Methyl 2-(2-nitrophenyl)acetate, the main research area is cyclization reduction nitrophenylpropanal; tandem reduction reductive amination nitrophenylpropanal; quinolinecarboxylate tetrahydro diastereoselective preparation; diastereoselective preparation tetrahydroquinolinecarboxylate.
A diastereoselective synthesis of cis-1-methyl-2-alkyl-1,2,3,4-tetrahydroquinoline-4-carboxylic acids and cis-2-alkyl-1,2,3,4-tetrahydroquinoline-4-carboxylic esters was developed from Me (2-nitrophenyl)acetate (I). The method involves alkylation of I with an allylic halide, ozonolysis of the double bond, and catalytic hydrogenation. The final hydrogenation initiates a tandem sequence involving reduction of the aromatic nitro group, condensation of the aniline or hydroxylamine nitrogen with the side chain carbonyl group, reduction of the resulting nitrogen intermediate, and reductive amination of the tetrahydroquinoline with formaldehyde produced in the ozonolysis to give a Me (±)-1-methyl-2-alkyl-1,2,3,4-tetrahydroquinoline-4-carboxylate. Removal of the formaldehyde prior to hydrogenation gives the simple (±)-2-alkyl derivatives The products were isolated in high yield as single diastereomers having the C-2 alkyl group cis to the C-4 carboxylic ester. The reaction was extended to the synthesis of tricyclic structures with similar high diastereoselection.
Journal of Organic Chemistry published new progress about Amination (intramol., stereoselective). 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, Recommanded Product: Methyl 2-(2-nitrophenyl)acetate.
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