- One-pot synthesis of 2-aminoquinoline-based alkaloids from acetonitrile
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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.
- Tomioka, Takashi,Takahashi, Yusuke,Maejima, Toshihide
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experimental part
p. 5113 - 5118
(2012/08/07)
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- A general and efficient 2-amination of pyridines and quinolines
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(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.
- Yin, Jingjun,Xiang, Bangping,Huffman, Mark A.,Raab, Conrad E.,Davies, Ian W.
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p. 4554 - 4557
(2008/02/04)
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- A short and versatile synthesis of 3-substituted 2-aminoquinolines
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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.
- Compagnone, Reinaldo S.,Suarez, Alirica I.,Zambrano, Jorge L.,Pina, Ivette C.,Dominguez, Jose N.
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p. 1631 - 1641
(2007/10/03)
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- The Chemistry of 5-Oxodihydroisoxazoles. XIV. Synthesis of 2-(1-Aryltetrazol-5-yl)propanoic Acids
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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.
- Caiazza, Daniela,Prager, Rolf H.,Schafer, Karl
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p. 1861 - 1872
(2007/10/03)
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- A simple new synthetic method for the preparation of 2-aminoquinolines
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2-Chloroquinolines (1a - j) heated in acetamide at 200° in the presence of potassium carbonate give 2-aminoquinolines (2a - j) in good yields.
- Korodi
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p. 1841 - 1846
(2007/10/02)
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