- Synthesis of 2,4,5-Trisubstituted Oxazoles with Complementary Regioselectivity from α-Oxoketene Dithioacetals and β-(Methylthio)-β-(het)aryl-2-propenones
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An efficient protocol for the synthesis of 2,5-substituted 4-acyloxazoles and the related 2,4-substituted 5-acyloxazoles with complementary regioselectivity from the corresponding α-oxoketene dithioacetals or β-(het)aryl/(methylthio)enone precursors has been reported. In the first protocol, the α-oxoketene dithioacetals or β-(methylthio)enones were converted to the corresponding α-bromo-β-(methylthio)enones followed by copper catalyzed inter/intramolecular annulation of these intermediates with various primary amides affording 2-(het)aryl/alkyl-4-(het)aroyl-5-(methylthio)/(het)aryloxazoles via concomitant formation of the C4-N and C5-O bond via enamide intermediates. In the second approach, the starting α-oxoketene dithioacetals or β-(methylthio)-β-(het)arylenones were subjected to base induced conjugate addition-elimination with various primary amides to furnish β-aroylenamides, which, on subsequent iodine catalyzed intramolecular oxidative C-H functionalization/C-O bond formation, afforded the corresponding regioisomeric 2-(het)aryl/alkyl-4-(methylthio)/(het)aryl-5-(het)aroyloxazoles in excellent yields. The methodology has also been extended for the synthesis of regioisomeric 4- or 5-aminooxazoles and 4- or 5-(n-butyl)oxazoles from the corresponding 4- or 5-(methylthio)oxazoles.
- Kumar, Siripuram Vijay,Acharya, Anand,Ila, Hiriyakkanavar
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- Transition metal free synthesis of multifunctional thiomethylated-benzenes from aryl/heteroaryl/cyclopropyl methyl ketones
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A base-promoted strategic synthesis of various functionalized thiomethylated-benzenes has been established from aryl/heteroaryl/cyclopropyl methyl ketone. We can directly access the thiomethylated-benzene nucleus embedded with diverse functional group by
- Panwar, Rahul,Althagafi, Ismail,Shally,Shaw, Ranjay,Elagamy, Amr,Shah, Chandan,Yadav, Pratik,Pratap, Ramendra
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- HETERO RING-FUSED PHENYL COMPOUNDS FOR INHIBITING TNIK AND MEDICAL USES THEREOF
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The present disclosure provides the compound having inhibitory property against TNIK having a specific chemical structure or its pharmaceutically acceptable salt. The present disclosure also provides a composition comprising the compound or its pharmaceutically acceptable salt. The present disclosure also provides a medical use of the compound, its salt or the composition comprising the compound or its pharmaceutically acceptable salt for treating or preventing cancer. The present disclosure also provides a method of treatment or prevention of cancer comprising administering the compound, its salt or the composition comprising the compound or its salt to a subject in need of such treatment or prevention.
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Paragraph 162-165
(2019/08/29)
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- Synthesis of Partially Reduced Imidazo[1,2- a ]pyridines through an Unprecedented Base-Mediated (4+2) Cyclization
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A water-mediated regioselective synthesis of 6,7-diaryl-5-oxo-2,3,5,6-tetrahydroimidazo[1,2-a]pyridine-6-carbonitriles was performed by the reaction of 2-[1-cyano-2,2-bis(methylsulfanyl)vinyl]benzonitrile with 1-aryl-2-(imidazolidin-2-ylidene)ethanones un
- Panwar, Rahul,Singh, Surjeet,Yadav, Pratik,Shaw, Ranjay,Kumar, Abhinav,Pratap, Ramendra
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p. 819 - 824
(2017/04/06)
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- Synthesis and molecular docking studies of novel 2-(2-amino-6-phenyl-4-pyrimidinylamino) ethanol derivatives: Using ring-opening reactions of cyclic ketene-N,O-acetal
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A series of six novel 2-(2-amino-6-phenyl-4-pyrimidinylamino) ethanol derivatives have been synthesized starting from commercially available substituted acetophenones via Oxoketene Dithioacetals with high yields. Ketene dithioacetal store act with 2-amino
- Kumar, G.M.V.N.A.R. Ravi,Thangamani, Arumugam
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p. 1555 - 1562
(2017/07/18)
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- Synthesis of β-amino-α,β-unsaturated ketone derivatives via sequential rhodium-catalyzed sulfur ylide formation/rearrangement
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In the presence of a Rh(II) catalyst and β-(methylthio)-α,β-unsaturated ketones, 1-sulfonyl-1,2,3-triazoles can be converted into functionalized β-amino-α,β-unsaturated ketones via formation of α-imino rhodium carbene/sulfur ylide and subsequent rearrangement. The products decompose to useful 2-methylthiopyrrole derivatives conveniently in high yield.
- He, Jun,Man, Zengming,Shi, Yinping,Li, Chuan-Ying
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p. 4816 - 4823
(2015/05/13)
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- Synthesis and anti-HCV determinant motif identification in pyranone carboxamide scaffold
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Hepatitis C Virus exhibits high genetic diversity. The current treatment for genotype-1 with ~80% sustained virologic responses is a combination of pegylated interferon, ribavirin and boceprevir/telaprevir/simeprevir which is associated with several side
- Balaraju, Tuniki,Konreddy, Ananda Kumar,Parveen, Afsana,Toyama, Massaki,Ito, Wataru,Karampuri, Srinivas,Baba, Masanori,Sharon, Ashoke,Bal, Chandralata
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supporting information
p. 5224 - 5227
(2015/11/09)
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- A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations
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A convenient base-mediated strategy to synthesize 3-aryol-4-methyl (or benzyl)-2-methylthio furans 2 (trisubstituted furans) has been developed through the domino coupling/annulations between available α-oxo ketene dithioacetals 1 and propargyl alcohols.
- Yang, Xiaobing,Hu, Fangzhong,Di, Hongjing,Cheng, Xinxin,Li, Dan,Kan, Xiaoli,Zou, Xiaomao,Zhang, Qichun
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supporting information
p. 8947 - 8951
(2014/12/11)
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- Copper-catalyzed trifluoromethylation of internal olefinic C-H bonds: Efficient routes to trifluoromethylated tetrasubstituted olefins and N-heterocycles
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The functionalization of internal olefins has been a challenging task in organic synthesis. Efficient CuII-catalyzed trifluoromethylation of internal olefins, that is, α-oxoketene dithioacetals, has been achieved by using Cu(OH)2 as a catalyst and TMSCF3 as a trifluoromethylating reagent. The push-pull effect from the polarized olefin substrates facilitates the internal olefinic C-H trifluoromethylation. Cyclic and acyclic dithioalkyl α-oxoketene acetals were used as the substrates and various substituents were tolerated. The internal olefinic C-H bond cleavage was not involved in the rate-determining step, and a mechanism that involves radicals is proposed based on a TEMPO-quenching experiment of the trifluoromethylation reaction. Further derivatization of the resultant CF 3 olefins led to multifunctionalized tetrasubstituted CF3 olefins and trifluoromethylated N-heterocycles.
- Mao, Zhifeng,Huang, Fei,Yu, Haifeng,Chen, Jiping,Yu, Zhengkun,Xu, Zhaoqing
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supporting information
p. 3439 - 3445
(2014/04/03)
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- Synthesis and anti-HCV activity of 4-hydroxyamino α-pyranone carboxamide analogues
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High genetic variability in hepatitis C virus (HCV), emergence of drug resistant viruses and side effects demand the requirement for development of new scaffolds to show an alternate mechanism. Herein, we report discovery of new scaffold I based on 4-hydr
- Konreddy, Ananda Kumar,Toyama, Massaki,Ito, Wataru,Bal, Chandralata,Baba, Masanori,Sharon, Ashoke
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supporting information
p. 259 - 263
(2014/04/03)
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- Base mediated synthesis of α-aminated aroyl/acetylnaphthalenes through [4+2] annulations
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We have developed a base promoted simple, efficient and alternative approach for the synthesis of 4-amino-3-aroyl//heteroaroyl/acetyl-2-methylsulfanyl-naphthalene-1-carbonitriles by reaction of easily accessible 3,3-bis(methylthio)-1-aryl/heteroaryl/acety
- Singh, Surjeet,Althagafi, Ismail,Yadav, Pratik,Panwar, Rahul,Kumar, Abhinav,Pratap, Ramendra
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p. 8879 - 8884
(2015/03/05)
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- One-pot straightforward approach to 2,3-disubstituted benzo/naphtho[b] furans via domino annulation of α-oxoketene dithioacetals and 1,4-benzo/naphthoquinone mediated by AlCl3 at room temperature
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A versatile and convenient one-pot direct approach to 2,3-disubstituted benzo/naphtho[b]furans via domino annulation of α-oxoketene dithioacetals and 1,4-benzo/naphthoquinone has been achieved in the presence of aluminium chloride at room temperature. Thi
- Verma, Girijesh Kumar,Verma, Rajiv Kumar,Shukla, Gaurav,Anugula, Nagaraju,Srivastava, Abhijeet,Singh, Maya Shankar
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p. 6612 - 6619
(2013/07/26)
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- Three-component synthesis of indanone-fused spirooxindole derivatives
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A simple, straightforward and versatile multicomponent protocol for the synthesis of indanone-fused spirooxindole derivatives has been developed. The strategy involves the one-pot three-component reaction of heterocyclic ketene aminals, 1H-indene-1,3(2H)-
- Chen, Xue-Bing,Liu, Xi-Ming,Huang, Rong,Yan, Sheng-Jiao,Lin, Jun
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supporting information
p. 4607 - 4613
(2013/07/26)
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- Synthesis of 2,4,6-trisubstituted pyrimidine and triazine heterocycles as antileishmanial agents
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A series of 2,4,6 trisubstituted pyrimidines and triazines have been synthesized and screened for its in vitro antileishmanial activity profile in promastigote model. Nine compounds have shown >94% inhibition against promastigotes at a concentration of 10
- Sunduru, Naresh,Agarwal, Anu,Katiyar, Sanjay Babu,Nishi,Goyal, Neena,Gupta, Suman,Chauhan, Prem M.S.
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p. 7706 - 7715
(2007/10/03)
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- Facile synthesis of 4-alkyl (and aryl)-2-aryl-6-diazo-4H-thieno[3,2-b] pyridine-5,7-diones
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Treatment of 3-{3-alkyl (and aryl)amino-5-arylthieno-2-yl}-2-diazo-3- oxopropanoates 8 with TMSOTf (3 equiv) in the presence of Et3N (6 equiv) in CH2Cl2 for 1 h at room temperature afforded 4-alkyl (and aryl)-2-aryl-6-diazo-4H-thieno
- Lee, Dong Joon,Kim, Kyongtae
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p. 4867 - 4869
(2007/10/03)
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- Synthesis of Dimethyl Oxazolidine and Tetrahydro-2H-1,3-oxazine Ring Substituted Ketene N,O-Acetals
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Dimethyl oxazolidine and tetrahydro-2H-1,3-oxazine ring substituted ketene N,O-acetals 3 and 4 were synthesized by the reaction of ketene S,S-acetals 2 with the corresponding amino alcohols.
- Huang, Zhi-Tang,Zhang, Ping-Cheng
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p. 1399 - 1407
(2007/10/02)
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- Synthesis, Reactions, and Tautomerism of Ketene N,S-Acetals with Benzothiazoline Ring
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Ketene dithioacetals 2 react with 2-aminothiophenol to afford the corresponding substituted 2(3H)-methylenebenzothiazoles 3.Some compounds 3 react with α,β-unsaturated esters to give 1H-pyridobenzothiazole derivatives 4 and 5 by an electrophilic addition and cyclocondensation sequence.
- Huang, Zhi-Tang,Shi, Xian
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p. 541 - 547
(2007/10/02)
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- SYNTHESIS OF CHIRAL HETEROCYCLIC KETENE N,O-ACETALS
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Chiral heterocyclic ketene N,O-acetals 3 were synthesized by the reaction of ketene mercaptals 2 with (R)-(-)-2-amino-1-butanol.
- Huang, Zhi-Tang,Zhang, Ping-Cheng
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p. 2999 - 3006
(2007/10/02)
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- Synthesis of Heterocyclic Ketene N,O-Acetals and Their Reactions with α,β-Unsaturated Esters
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Ketene dithioacetals 2 react with 2-aminoethanol or 1-amino-2-propanol to afford the corresponding substituted 2-methyleneoxazolidines 3 and 4.In some cases, 3 and 4 react with α,β-unsaturated esters to give 5H-oxazolopyridine derivatives 5 by an e
- Huang, Zhi-Tang,Zhang, Ping-Cheng
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p. 2011 - 2016
(2007/10/02)
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- SYNTHESIS OF BENZOYL SUBSTITUTED HETEROCYCLIC KETENE AMINALS BY CONDENSATION OF BENZOYL KETENE MERCAPTALS WITH DIAMINES
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2-(Benzoylmethylene)imidazolidines 2 and 5, -hexahydropyrimidines 3 and 6, or -hexahydro-1H-1,3-diazepines 4 were synthesized by the reaction of benzoyl substituted ketene mercaptals 1 with diamines.
- Huang, Zhi-tang,Liu, Zhi-rong
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p. 943 - 958
(2007/10/02)
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- Method of making known and previously unavailable pyrylium salts
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A method is disclosed for preparing pyrylium and thiapyrylium salts having the formula represented below (where X is O,S or Se): STR1 and where R1 and R2 represents a branched or unbranched alkyl radical having up to about 15 carbon
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- Synthesis of 2,6-Disubstituted Pyridines, Polypyridinyls, and Annulated Pyridines
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1,5-Enediones containing a variety of substituents in the 1,5-positions are formed in good yields by the reaction of methyl ketone enolates, generated with potassium tert-butoxide, with α-oxoketene dithioacetals, the latter being prepared from alkyl, cycloalkyl, aryl, or heteryl methyl ketones, NaH, CS2, and CH3I.Ring closure of the 1,5-enediones with NH4OAc gave 2,6-disubstituted 4-(methylthio)pyridines in good to excellent yields.This procedure is particularly suited for the synthesis of 2,6-diheterylpyridines and provides a simple synthesis of terpyridinyl and other oligopyridines.The methylthio groups in the α-oxoketene dithioacetals may be oxidized to the mono- and disulfoxides with m-chloroperbenzoic acid, but with excess peracid, in addition to oxidation to the disulfone, epoxidation of the double bond also occurs.The pyridine 4-methylthio substituent may also be oxidized to the sulfoxide and to the sulfone, and the latter may be displaced with cyanide ion to form the corresponding 4-carbonitrile.
- Potts, Kevin T.,Cipullo, Michael J.,Ralli, Philip,Theodoridis, George
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p. 3027 - 3038
(2007/10/02)
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