63403-55-4Relevant academic research and scientific papers
Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds
Chang, Xiao-Yong,Chen, Ji-Jun,Gu, Qiang-Shuai,Jiang, Sheng-Peng,Li, Zhong-Liang,Liu, Lin,Liu, Xiao-Dong,Liu, Xin-Yuan,Su, Xiao-Long,Wang, Fu-Li,Yang, Chang-Jiang,Ye, Liu
supporting information, p. 380 - 384 (2020/10/30)
The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.
Photochemistry of substituted propiophenones: An interesting α-and aryl substituents effect on their photobehaviour
Sonawane, Harikisan R.,Bellur, Nanjundiah S.,Nazeruddin
, p. 11281 - 11294 (2007/10/02)
Photochemistry of different α-substituted and phenyl-substituted propiophenones in methanol is investigated with a view to delineate the substituent effect with a special reference tu their rearrangement to α-arylpropanoic acids, an important class of nonsteroidal antiinflammatory agents. The results thus obtained bringsforth an important element of their reactivityprofile i.e. the α-chloro-substituent in combination with nuclear alkyl substituents (para>meta) favours 1,2-arylmigration leading to the synthetically useful reaction for α-arylpro panoic acids.
An efficient synthesis of fenoprofen, an important antiinflammatory agent
Sonawane, H. R.,Nanjundiah, B. S.,Nazeruddin, G. M.
, p. 705 - 706 (2007/10/02)
A simple and practical synthesis of (+/-)-fenoprofen, a well-known non-steroidal antiinflammatory agent, from the commercially available m-phenoxybenzaldehyde has been described.
Manufacture of alpha-arylalkanoic acids and precursors
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, (2008/06/13)
α-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an α-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the α-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding α-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding α-arylalkanoic acid.
