221285-25-2Relevant academic research and scientific papers
Heavy-Atom Tunneling Through Crossing Potential Energy Surfaces: Cyclization of a Triplet 2-Formylarylnitrene to a Singlet 2,1-Benzisoxazole
Fausto, Rui,McMahon, Robert J.,Nunes, Cláudio M.,Roque, José P. L.,Viegas, Luís P.,Wood, Samuel A.
supporting information, p. 17622 - 17627 (2020/08/14)
Not long ago, the occurrence of quantum mechanical tunneling (QMT) chemistry involving atoms heavier than hydrogen was considered unreasonable. Contributing to the shift of this paradigm, we present here the discovery of a new and distinct heavy-atom QMT
A [4 + 3] Annulation Reaction of aza- o-Quinone Methides with Arylcarbohydrazonoyl Chlorides for Synthesis of 2,3-Dihydro-1 H-benzo[ e][1,2,4]triazepines
Guo, Zhenyan,Jia, Hao,Liu, Honglei,Wang, Qijun,Huang, Jiaxing,Guo, Hongchao
supporting information, p. 2939 - 2943 (2018/05/28)
An unprecedented [4 + 3] annulation reaction of aza-ortho-quinone methides with arylcarbohydrazonoyl chlorides has been achieved under mild conditions. The annulation underwent a sequential conjugate addition/intramolecular annulation/rearrangement, providing a useful method for the synthesis of biologically interesting 2,3-dihydro-1H-benzo[e][1,2,4]triazepine.
Pd-Catalyzed Three-Component Domino Reaction of Vinyl Benzoxazinanones for Regioselective and Stereoselective Synthesis of Allylic Sulfone-Containing Amino Acid Derivatives
Hao, Jiping,Xu, Yi,Xu, Zhongliang,Zhang, Zhiqiang,Yang, Weibo
supporting information, p. 7888 - 7892 (2019/01/04)
A Pd-catalyzed, highly regioselective and stereoselective three-component domino allylic substitution/N-H carbene insertion reaction under mild conditions is described. This reaction demonstrates a wide substrate scope and satisfactory functional group tolerance, providing a broad range of allylic sulfone-containing amino acid derivatives. Moreover, DBU mediates highly diastereoselective cross-dehydrogenative coupling annulation of allylic sulfones without using peroxides or any metal oxidants. This developed protocol affords 7-membered ring heterocyclic compounds incorporating both sulfone-containing amino acid esters and one quaternary carbon center. Mechanistic studies indicate that an unusual umpolung of glycine occurred in this annulation.
Catalytic Asymmetric Construction of the Tryptanthrin Skeleton via an Enantioselective Decarboxylative [4 + 2] Cyclization
Mei, Guang-Jian,Bian, Chen-Yu,Li, Guo-Hao,Xu, Shao-Li,Zheng, Wen-Qin,Shi, Feng
supporting information, p. 3219 - 3222 (2017/06/23)
The first catalytic asymmetric construction of the tryptanthrin skeleton has been established, taking advantage of a palladium(0)/chiral ligand-catalyzed enantioselective decarboxylative [4 + 2] cyclization of vinyl benzoxazinanones with isatins. This rea
Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: Synthesis of quinazolines by trapping of ammonia
Gopalaiah, Kovuru,Saini, Anupama,Devi, Alka
, p. 5781 - 5789 (2017/07/22)
A novel approach to construct 2-aryl/heteroaryl quinazolines was developed through an iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines under aerobic oxidative conditions. The reaction proceeds via the formation of N-benzylideneb
Tandem [3 + 2] cycloaddition/1,4-addition reaction of azomethine ylides and aza-o-quinone methides for asymmetric synthesis of imidazolines
Jia, Hao,Liu, Honglei,Guo, Zhenyan,Huang, Jiaxing,Guo, Hongchao
supporting information, p. 5236 - 5239 (2017/11/06)
An enantioselective synthesis of biologically important imidazolidines has been achieved via a tandem [3 + 2] cycloaddition/1,4-addition reaction of azomethine ylide and aza-o-quinone methides. With the use of this tool, various imidazolidine derivatives are obtained in good yields with excellent diastereoselectivities and enantioselectivities.
N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles
Hovey, M. Todd,Check, Christopher T.,Sipher, Alexandra F.,Scheidt, Karl A.
supporting information, p. 9603 - 9607 (2014/10/15)
A convergent and efficient transition-metal-free catalytic synthesis of 2-aryl-indoles has been developed. The interception of a highly reactive and transient aza-ortho-quinone methide by an acyl anion equivalent generated through N-hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported. Umpolung: N-heterocyclic carbene catalysis is used for the convergent and efficient transition-metal-free synthesis of 2-aryl-indoles. The interception of a highly reactive and transient aza-ortho-quinone methide by an acyl anion equivalent is central to this successful strategy. The reaction exhibits high yields and a wide scope, and it has been applied to a streamlined synthesis of a kinase inhibitor.
HETEROCYCLIC COMPOUNDS AND THEIR USE AS INHIBITORS OF PI3K ACTIVITY
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Page/Page column 99-100, (2012/01/15)
Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorde
Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands
Ida, Yoshihiro,Matsubara, Ayaka,Nemoto, Toru,Saito, Manabu,Hirayama, Shigeto,Fujii, Hideaki,Nagase, Hiroshi
, p. 5810 - 5831 (2012/11/06)
We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.
HYDROXYQUINOLIN-2(1H)-ONES AND DERIVATIVES THEREOF
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Page/Page column 59-60, (2010/07/10)
This invention relates to known and novel hydroxyquinolin-2(1H)-ones and derivatives thereof which are useful for the treatment of cognitive-related disorders and neuropathic pain disorders in a mammal, e.g., a human. The invention also relates to pharmaceutical compositions containing such compounds.
