- Visible-light-induced radical isocyanide insertion protocol for the synthesis of difluoromethylated spiro[indole-3,3′-quinoline] derivatives
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Herein, we report the first protocol for visible-light-induced radical isocyanide insertion reactions between 3-(2-isocyanobenzyl)-indoles and bromodifluoroacetates or bromodifluoroacetamides. The protocol, which has good functional group tolerance and a broad substrate scope, constitutes an efficient and general route to difluoromethylated spiro[indole-3,3′-quinoline] derivatives. This journal is
- Zhang, Jingjing,Xu, Wentao,Qu, Yi,Liu, Yuxiu,Li, Yongqiang,Song, Hongjian,Wang, Qingmin
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supporting information
p. 15212 - 15215
(2020/12/21)
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- Highly Diastereoselective Synthesis of Trifluoromethyl Indolines by Interceptive Benzylic Decarboxylative Cycloaddition of Nonvinyl, Trifluoromethyl Benzoxazinanones with Sulfur Ylides under Palladium Catalysis
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A highly diastereoselective synthesis of trifluoromethyl-substituted indolines under palladium catalysis is disclosed. The reaction proceeds by interceptive decarboxylative benzylic cycloaddition (IDBC) of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides. The palladium-π-benzyl zwitterionic intermediates are suggested for this transformation, and this would be the first example of an IDBC reaction.
- Punna, Nagender,Das, Pulakesh,Gouverneur, Véronique,Shibata, Norio
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supporting information
p. 1526 - 1529
(2018/03/23)
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- Pd-Catalyzed Three-Component Domino Reaction of Vinyl Benzoxazinanones for Regioselective and Stereoselective Synthesis of Allylic Sulfone-Containing Amino Acid Derivatives
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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.
- Hao, Jiping,Xu, Yi,Xu, Zhongliang,Zhang, Zhiqiang,Yang, Weibo
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supporting information
p. 7888 - 7892
(2019/01/04)
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- Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes
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A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.
- Zhang, Song-Lin,Deng, Zhu-Qin
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supporting information
p. 8966 - 8970
(2016/10/05)
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- Decarboxylative [4+2] Cycloaddition by Synergistic Palladium and Organocatalysis
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A novel reaction based on synergistic catalysis, combining palladium- and organocatalysis has been developed. The palladium catalyst activates vinyl benzoxazinanones via a decarboxylation to undergo a [4+2] cycloaddition with iminium-ion activated α,β-uns
- Leth, Lars A.,Glaus, Florian,Meazza, Marta,Fu, Liang,Th?gersen, Mathias K.,Bitsch, Emma A.,J?rgensen, Karl Anker
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supporting information
p. 15272 - 15276
(2016/12/03)
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- Synthesis of polysubstituted cyclopenta[b]indoles via relay gold(i)/Bronsted acid catalysis
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An efficient relay catalytic process involving Au(i)/Bronsted acid to access various polysubstituted cyclopentannulated indoles from easily accessible 1-(2-aminophenyl)prop-2-ynols and readily available 1,3-dicarbonyls has been developed. In an unprecedented event, the intermediate 2-indolylmethyl cations undergo the cation-Ene reaction with various 1,3-dicarbonyls followed by an intramolecular Friedel-Crafts-type reaction generating functionalized cyclopenta[b]indoles. This journal is
- Dhiman, Seema,Ramasastry
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supporting information
p. 557 - 560
(2015/01/09)
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- Cycloadditions with Bromo-Substituted Morita-Baylis-Hillman Adducts of Isatins and N-(ortho-Chloromethyl)aryl Amides
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Efficient construction of a challenging aza-spirocycloheptane oxindole scaffold is reported through an unprecedented [4 + 3] cycloaddition reaction with bromo-substituted Morita-Baylis-Hillman adducts of isatins and N-(ortho-chloromethyl)aryl amides. Both reactive intermediates, the allylic phosphonium ylides and aza-o-quinone methides, were in situ generated, chemoselectively facilitated by a Lewis base and Bronsted base, respectively.
- Zhan, Gu,Shi, Ming-Lin,He, Qing,Du, Wei,Chen, Ying-Chun
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supporting information
p. 4750 - 4753
(2015/10/12)
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- N-Heterocyclic Carbene-Catalyzed Synthesis of 2-Aryl Indoles
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Transition metal-free catalytic methods for access to 2-arylindole compounds.
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Paragraph 0035-0036; 0042-0043
(2015/11/27)
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- N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles
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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.
- Hovey, M. Todd,Check, Christopher T.,Sipher, Alexandra F.,Scheidt, Karl A.
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supporting information
p. 9603 - 9607
(2014/10/15)
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- Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands
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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.
- Ida, Yoshihiro,Matsubara, Ayaka,Nemoto, Toru,Saito, Manabu,Hirayama, Shigeto,Fujii, Hideaki,Nagase, Hiroshi
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p. 5810 - 5831
(2012/11/06)
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- HCV INHIBITORS AND METHODS OF USING THEM
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The present invention comprises tetrazoloquinoline-compounds that are inhibitors of HCV. Compositions comprising the compounds in combination with a pharmaceutically acceptable carrier are also disclosed, as are methods of using the compounds and composit
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Page/Page column 20
(2010/02/11)
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- Novel quinolinone-phosphonic acid AMPA antagonists devoid of nephrotoxicity.
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We reported previously the synthesis and structure-activity relationships (SAR) in a series of 2-(1H)-oxoquinolines bearing different acidic functions in the 3-position. Exploiting these SAR, we were able to identify 6,7-dichloro-2-(1H)-oxoquinoline-3-phosphonic acid compound 3 (S 17625) as a potent, in vivo active AMPA antagonist. Unfortunately, during the course of the development, nephrotoxicity was manifest at therapeutically effective doses. Considering that some similitude exists between S 17625 and probenecid, a compound known to protect against the nephrotoxicity and/or slow the clearance of different drugs, we decided to synthesise some new analogues of S 17625 incorporating some of the salient features of probenecid. Replacement of the chlorine in position 6 by a sulfonylamine led to very potent AMPA antagonists endowed with good in vivo activity and lacking nephrotoxicity potential. Amongst the compounds evaluated, derivatives 7a and 7s appear to be the most promising and are currently evaluated in therapeutically relevant stroke models.
- Cordi, Alex A,Desos, Patrice,Ruano, Elisabeth,Al-Badri, Hashim,Fugier, Claude,Chapman, Astrid G,Meldrum, Brian S,Thomas, Jean-Yves,Roger, Anita,Lestage, Pierre
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p. 787 - 802
(2007/10/03)
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- Synthesis and structure-activity relationship studies of conformationally restricted, analogs of 2-chloro-4-trifluoromethylpyrimidine- 5-[N-(3',5'-bis(trifluoromethyl)phenyl)]carboxamide
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2-Chloro-4-trifluoromethylpyrimidine-5-N[(3,5- bis(trifluoromethyl)phenyl] carboxamide (1) was identified as an inhibitor of AP-1 and NF-κB mediated transcriptional activation. In an effort to identify novel compounds that contain less number of trifluoromethyl groups with comparable potency as 1, several conformationally restricted analogs of I were synthesized in which the pyrimidine ring and the aniline ring were connected through a second 'bridge'. The 7-membered sulfur bridged analog was the most potent in this series, and comparable to 1 in activity.
- Palanki, Moorthy S.S.,Erdman, Paul E.,Goldman, Mark E.,Suto, Carla,Suto, Mark J.
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