66598-81-0Relevant academic research and scientific papers
Meta C-H Arylation of Electron-Rich Arenes: Reversing the Conventional Site Selectivity
Liu, Luo-Yan,Qiao, Jennifer X.,Yeung, Kap-Sun,Ewing, William R.,Yu, Jin-Quan
supporting information, p. 14870 - 14877 (2019/10/02)
Controlling site selectivity of C-H activation without using a directing group remains a significant challenge. While Pd(II) catalysts modulated by a mutually repulsive pyridine-type ligand have been shown to favor the relatively electron-rich carbon centers of arenes, reversing the selectivity to favor palladation at the relatively electron-deficient positions has not been possible. Herein we report the first catalytic system that effectively performs meta C-H arylation of a variety of alkoxy aromatics including 2,3-dihydrobenzofuran and chromane with exclusive meta site selectivity, thus reversing the conventional site selectivity governed by native electronic effects. The identification of an effective ligand and modified norbornene (NBE-CO2Me), as well as taking advantage of the statistics, are essential for achieving the exclusive meta selectivity.
Planar chiral [2.2]paracyclophane-based bisoxazoline ligands: Design, synthesis, and use in cu-catalyzed inter- and intramolecular asymmetric O-H insertion reactions
Kitagaki, Shinji,Murata, Shunsuke,Asaoka, Kisaki,Sugisaka, Kenta,Mukai, Chisato,Takenaga, Naoko,Yoshida, Keisuke
, p. 1006 - 1014 (2018/10/08)
Centrally chiral bisoxazolines connected directly to a planar chiral [2.2]paracyclophane backbone were synthesized and evaluated as asymmetric ligands in Cu-catalyzed intermolecular ethanolic O-H insertion reactions of α-diazo esters. The reactivities and enantioselectivities of Cu complexes of the synthesized bisoxazoline ligands were lower than those of ligands without central chirality. However, planar chiral [2.2] paracyclophane-based bisoxazoline ligands with an inserted benzene spacer that had a sterically demanding isopropyl substituent showed good enantioselectivities in inter- and intramolecular aromatic O-H insertion reactions, without the aid of central chirality.
An efficient and practical enantiospecific synthesis of methyl chromanone- and chroman-2-carboxylates
Kim, Dong Woon,Maqusood Alam,Lee, Young Hun,Khan, M. Naseer A.,Zhang, Yong,Lee, Yong Sup
, p. 912 - 917 (2015/08/24)
Chromanone-2-carboxylates and chroman-2-carboxylates are useful building blocks for the synthesis of a variety of bioactive compounds, such as repinotan, fidarestat, and nebivolol. An efficient and practical enantiospecific synthesis of chromanone-2-carboxylates and chroman-2-carboxylates has been accomplished using intramolecular Mitsunobu etherification of methyl (S)-2-hydroxy-4-oxo-4-(2′-hydroxy)phenylbutanoates derived from l-malic acid.
NEW SOMATOSTATIN RECEPTOR SUBTYPE 4 (SSTR4) AGONISTS
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Page/Page column 143, (2014/12/12)
The invention relates to 3-aza-bicyclo[3.1.0]hexane-6-carboxylic acid amide derivatives of general formula (I), which are agonists of somatostatin receptor subtype 4 (SSTR4), useful for preventing or treating medical disorders related to SSTR4. In addition, the invention relates to processes for preparing pharmaceutical compositions as well as processes for manufacture of the compounds according to the invention.
New Somatostatin receptor subtype 4 (SSTR4) agonists
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Paragraph 0572; 0573; 0574; 0575, (2014/12/09)
3-aza-bicyclo[3.1.0]hexane-6-carboxylic acid amide derivatives which are agonists of somatostatin receptor subtype 4 (SSTR4), useful for preventing or treating medical disorders related to SSTR4.
Enantioselective copper-catalyzed intramolecular phenolic O-H bond insertion: Synthesis of chiral 2-carboxy dihydrobenzofurans, dihydrobenzopyrans, and tetrahydrobenzooxepines
Song, Xiao-Guang,Zhu, Shou-Fei,Xie, Xiu-Lan,Zhou, Qi-Lin
, p. 2555 - 2558 (2013/04/10)
Efficient: A copper-catalyzed enantioselective intramolecular insertion of carbenoids into phenolic O-H bonds has been developed. This method can be used for the synthesis of the title compounds in high yields and excellent enantioselectivities under mild and neutral conditions (see scheme). NaBAr F=sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Copyright
CHROMANE AND CHROMENE DERIVATIVES AND USES THEREOF
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Page/Page column 59-62, (2010/11/28)
Methods of preparing compounds of formula (I) or pharmaceutically acceptable salts thereof are provided wherein each of R1, R2, R3, R4, x, m, n, and Ar are as defined, and described in classes and subclasses herein, which are agonists or partial agonists of the 2C subtype of brain serotonin receptors. The compounds, and compositions containing the compounds, can be used to treat a variety of central nervous system disorders such as schizophrenia.
Fused bicyclic carboxamide derivatives and methods of their use
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Page/Page column 39, (2010/02/11)
Fused bicyclic carboxamide derivatives are disclosed. Pharmaceutical compositions containing the compounds and methods for their use are also disclosed.
Potent and highly selective kappa opioid receptor agonists incorporating chroman- and 2,3-dihydrobenzofuran-based constraints
Chu, Guo-Hua,Gu, Minghua,Cassel, Joel A.,Belanger, Serge,Graczyk, Thomas M.,Dehaven, Robert N.,Conway-James, Nathalie,Koblish, Mike,Little, Patrick J.,DeHaven-Hudkins, Diane L.,Dolle, Roland E.
, p. 5114 - 5119 (2007/10/03)
Two novel chemical classes of kappa opioid receptor agonists, chroman-2-carboxamide derivatives and 2,3-dihydrobenzofuran-2-carboxamide derivatives, were synthesized. These agents exhibited high and selective affinity for the kappa opioid receptor.
Hydrogenated 1-benzooxacycloalkylpyridinecarboxylic acid compounds
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, (2008/06/13)
The invention relates to novel hydrogenated 1-benzooxacycloalkylpyridinecarboxylic acid compounds of formula STR1 in which the variable R1, R2, R3, R4, R5, alk, X, Z, m, n and p, the dotted line and t
