74844-99-8

Usage

InChI:InChI=1/C10H10N2/c1-7-6-8-4-2-3-5-9(8)12-10(7)11/h2-6H,1H3,(H2,11,12)

Upstream product

• 57876-69-4 2-chloro-3-methyl-quinoline 
• 1873-55-8 3-methylquinoline N-oxide 
• 74845-05-9 o-nitro-α-methylcinnamonitrile 
• 552-89-6 2-nitro-benzaldehyde 
• 74845-05-9 (R,S)-2-cyano-3-(2'-nitrophenyl)propene 
• 145771-21-7 2-(3-Methyl-quinolin-2-yl)-5-oxo-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester 
• 74844-95-4 (Z)-3-(2-Amino-phenyl)-2-methyl-acrylonitrile 

Relevant academic research and scientific papers

One-pot synthesis of 2-aminoquinoline-based alkaloids from acetonitrile

α-Diaminoboryl carbanions, readily prepared from acetonitrile, stereoselectively convert 2-nitrobenzaldehydes into nitrophenyl (Z)-acrylonitriles. Subsequent reductive cyclization leads to a series of 2-aminoquinoline derivatives. The entire procedure is practically operated in a single flask.

A general and efficient 2-amination of pyridines and quinolines

(Chemical Equation Presented) Pyridine N-oxides were converted to 2-aminopyridines in a one-pot fashion using Ts2O-t-BuNH2 followed by in situ deprotection with TFA. The amination proceeded in high yields, excellent 2-/4-selectivity, and with good functional group compatibility. 2-Amino (iso)quinolines were also obtained in the same manner. Combined with the simple oxidation of pyridines to pyridine N-oxides, this method provides a general and efficient way for amination of 2-unsubstituted pyridines.

A short and versatile synthesis of 3-substituted 2-aminoquinolines

A short and versatile synthesis of a series of 3-substituted 2-aminoquinolines was accomplished in good yields starting from 2-nitrobenzaldehyde. Organic phosphonates were used as key synthetic intermediates and in some cases amino acids as readily available starting materials. The final two key steps of the sequence involving a reduction and ring closure that led to the 2-aminoquinoline skeleton were carried out in a 'one pot' procedure using SnCL22H2O.

The Chemistry of 5-Oxodihydroisoxazoles. XIV. Synthesis of 2-(1-Aryltetrazol-5-yl)propanoic Acids

A number of N-arylisoxazol-5(2H)-ones (aryl = phenyl, isoquinolin-1-yl, quinolin-2-yl, 2-phenylquinazolin-4-yl and benzothiazol-2-yl) have been reacted with lithium azide to give 2-(1-aryltetrazol-5-yl)acetic esters, which have been C-methylated and hydrolysed.The resulting 2-(1-aryltetrazol-5-yl)propanoic acid had low antiinflammatory activity, as judged by inhibition of synthesis of prostaglandin PGE2 or tumor necrosis factor α.

A simple new synthetic method for the preparation of 2-aminoquinolines

2-Chloroquinolines (1a - j) heated in acetamide at 200° in the presence of potassium carbonate give 2-aminoquinolines (2a - j) in good yields.