ChemInform Abstract: Trifluoroacetic Acid Mediated Intramolecular Formal N-H Insertion Reactions with Amino-α-diazoketones: A Facile and Efficient Synthesis of Optically Pure Pyrrolidinones and Piperidinones.

ChemInform ◽  
2000 ◽  
Vol 31 (49) ◽  
pp. no-no
Author(s):  
Hua Yang ◽  
Valdas Jurkauskas ◽  
Nicole Mackintosh ◽  
Tobias Mogren ◽  
Corey R. J. Stephenson ◽  
...  
2000 ◽  
Vol 78 (6) ◽  
pp. 800-808 ◽  
Author(s):  
Hua Yang ◽  
Valdas Jurkauskas ◽  
Nicole Mackintosh ◽  
Tobias Mogren ◽  
Corey RJ Stephenson ◽  
...  

Trifluoroacetic acid (TFA) was found to promote intramolecular formal N-H insertion reactions. Upon treatment with TFA, optically pure N-Boc-β'-amino-α-diazoketones (5a-c) and N-Boc-γ'-amino-α-diazoketones (10a-d) can be converted, with retention of chirality, into pyrrolidinones (11a-c) and piperidinones (12a-d), respectively, with concomitant removal of the Boc group, in good to excellent yields.Key words: α-diazoketone, amino acid, pyrrolidinone, piperidinone, N-H insertion.


ChemInform ◽  
2010 ◽  
Vol 26 (39) ◽  
pp. no-no
Author(s):  
S. NAKAMURA ◽  
M. KONDO ◽  
K. GOTO ◽  
S. NAITO ◽  
Y. TSUDA ◽  
...  

Synthesis ◽  
2008 ◽  
Vol 2008 (15) ◽  
pp. 2391-2397 ◽  
Author(s):  
Bernd Clement ◽  
Dennis Schade ◽  
Jürke Kotthaus

2002 ◽  
Vol 55 (4) ◽  
pp. 287 ◽  
Author(s):  
L. W. Deady ◽  
D. Ganame ◽  
N. H. Quazi ◽  
S. D. Zanatta

The reaction of N-(pyridin-3-yl) and -4-yl thiourea derivatives with malonyl dichloride in trifluoroacetic acid is shown to be an efficient synthesis of the corresponding thiobarbituric acids. The pyridin-2-yl analogue cleaved and produced, instead, 2-hydroxy-4H-pyrido[1,2a]pyrimidin-4-one.


2020 ◽  
Vol 840 ◽  
pp. 251-256 ◽  
Author(s):  
Phan Thi Thanh Nga ◽  
Masaya Tone ◽  
Hayato Inoue ◽  
Kazutaka Shibatomi ◽  
Seiji Iwasa

Oxindole derivatives were efficiently synthesized from diazoamides derived from aniline derivatives in the presence of a Ru(II)-Pheox catalyst. Ru(II)-Pheox was found to be one of the most efficient catalysts so far for the synthesis of oxindole derivatives from the diazoamides in high yields (up to 99%) with high regioselectivity. Furthermore, the reaction was rapid and no substituent effects on the aromatic ring.


1996 ◽  
Vol 61 (26) ◽  
pp. 9635-9635
Author(s):  
Hiroki Hamada ◽  
Mizuho Shiromoto ◽  
Makoto Funahashi ◽  
Toshiyuki Itoh ◽  
Kaoru Nakamura

ChemistryOpen ◽  
2015 ◽  
Vol 4 (4) ◽  
pp. 483-488 ◽  
Author(s):  
Xi Chen ◽  
Ting Mei ◽  
Yunfeng Cui ◽  
Qijia Chen ◽  
Xiangtao Liu ◽  
...  

2021 ◽  
Vol 18 ◽  
Author(s):  
D.E. Prasada Rao ◽  
M. David Raju ◽  
J. Surendra ◽  
A. Vasu Babu ◽  
P. Eswaraiah ◽  
...  

An efficient synthetic route for the novel bis-imdizo[1,2-a]pyridine-3-yl)methane (2a-k) derivatives have been developed using acetic acid and two drops of trifluoroacetic acid at 40-45oC, resulting in 60-72% yields. An attempt to synthesize bis(Imidazo[1,2-a]pyridin-3-yl)methyl chloride derivatives by the reaction between two moles of imidazo[1,2-a]pyridine, one mole of chloroacetaldehyde in acetic acid, and two drops of trifluoroacetic acid was not successful, instead underwent dehydrohalogenation to yield vinyl derivatives (4a-d).


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