- Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds
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An organocatalytic vinylogous Michael addition triggered triple-cascade reaction has been developed. 2-Hydroxycinnamaldehydes worked under iminium activation with either acyclic or cyclic ketone-derived α,α-dicyanoalkenes, yielding the benzofused oxabicyclo[3.3.1]nonanes bearing one quaternary stereocenter with excellent stereoselectivities.
- Wu, Hui-Chun,Wang, Chen,Chen, Ying-Han,Liu, Yan-Kai
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supporting information
p. 1762 - 1765
(2021/02/27)
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- Synthesis, in vivo anti-inflammatory, COX-1/COX-2 and 5-LOX inhibitory activities of new 2,3,4-trisubstituted thiophene derivatives
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New series of thiophene derivatives were synthesized and evaluated for their in vivo anti-inflammatory activity using carrageenan-induced paw edema model. The most active in vivo anti-inflammatory compounds 5b, 11b, 14c, 18c, 19c and 20d were further evaluated for their in vitro COX-1/COX-2 and 5-LOX inhibitory activities. The in vitro assay results revealed that the N-(4-(4-chlorophenyl)-3-cyanothiophen-2-yl)-2-morpholinoacetamide (5b) possesses the highest selectivity toward COX-2 (IC50 = 5.45 μM) with selectivity index value of 8.37 compared to celecoxib with COX-2 selectivity index value of 15.44. In addition, it showed acceptable 5-LOX inhibitory activity (IC50 = 4.33 μM) compared to NDGA (IC50 = 2.46 μM). Molecular modeling study was conducted to study the postulated binding of compound 5b into the active site of COX-2 and 5-LOX, and it revealed that 5b binds similarly to celecoxib and NDGA, respectively. Overall, the morpholinoacetamide-thiophene hybrid 5b could serve as a promising lead for further development of new potent anti-inflammatory agents that act as dual COX-2/5-LOX inhibitors.
- Qandeel, Nermeen A.,El-Damasy, Ashraf K.,Sharawy, Maha H.,Bayomi, Said M.,El-Gohary, Nadia S.
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- A [5 + 1] annulation strategy for the synthesis of multifunctional biaryls and: P -teraryls from 1,6-Michael acceptor ketene dithioacetals
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A new type of ketene dithioacetal, 2-(3,3-bis-methylsulfanyl-1-arylallylidene)malononitriles containing 1,4 and 1,6-Michael acceptors, were synthesized to study their reactivity for the synthesis of a new molecular entity. We report a [5 + 1] annulation s
- Althagafi, Ismail,Elagamy, Amr,Kumar, Abhinav,Pratap, Ramendra,Shally,Shaw, Ranjay
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p. 6407 - 6417
(2020/09/07)
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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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- "on Water" Direct Catalytic Vinylogous Aldol Reaction of Silyl Glyoxylates
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The unique reactivity of water in the direct catalytic vinylogous aldol reaction of silyl glyoxylates is reported. With the hydrogen-bonding networks from water, the unfavorable homogeneous reactions in organic solvents were severely suppressed, and the "
- Pan, Hong,Han, Man-Yi,Li, Pinhua,Wang, Lei
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p. 14281 - 14290
(2019/11/03)
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- Chemoselective synthesis of m-teraryls through ring transformation of 2 H-pyran-2-ones by 2-(1-arylethylidene)-malononitriles
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We have developed a simple, efficient and chemoselective approach for the synthesis of m-teraryls by the reaction of 6-aryl-2-oxo-4-(sec.amino)-2H-pyran-3-carbonitriles and 2-(1-arylethylidene)malononitriles under basic conditions. We used 6-aryl-2-oxo-4-
- Panwar, Rahul,Shally,Shaw, Ranjay,Elagamy, Amr,Pratap, Ramendra
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p. 8994 - 9002
(2018/12/10)
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- Syntheses of donor-acceptor-functionalized dihydroazulenes
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The dihydroazulene (DHA)/vinylheptafulvene (VHF) photo/thermoswitch has been of interest for use in molecular electronics and advanced materials. The switching between the two isomers has previously been found to depend strongly on the presence of donor a
- Broman, Soren Lindbaek,Jevric, Martyn,Bond, Andrew D.,Nielsen, Mogens Brondsted
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- Phosphine-catalyzed domino reaction: A novel sequential [2+3] and [3+2] annulation reaction of γ-substituent allenoates to construct bicyclic[3, 3, 0]octene derivatives
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We have successfully developed a novel and efficient phosphine-catalyzed sequential [2+3] and [3+2] annulation reaction of γ-substituent allenoates to construct bicyclic[3, 3, 0]octene derivatives. The protocol uses readily available γ-substituent allenoa
- Li, Erqing,Huang, You
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supporting information
p. 948 - 950
(2014/01/06)
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- Solventless convenient synthesis of new cyano-2-aminopyridine derivatives from enaminonitriles
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A synthesis of novel 4-substituted-3-cyano-2-aminopyridines using enaminonitriles and various primary amines was established under microwave irradiation and solvent-free conditions. Structures of the new compounds were characterized by IR, MS, 1/sup
- Villemin, Didier,Belhadj, Zahira,Cheikh, Nawel,Choukchou-Braham, Noureddine,Bar, Nathalie,Lohier, Jean-Fran?ois
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p. 1664 - 1668
(2013/03/28)
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- Basic ionic liquid as catalyst for the efficient and green synthesis of 2-amino-3-nitrobenzonitriles in ethanol
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A basic ionic liquid, [BmIm]OH was used as catalyst in the cyclocondensation of various kinds of vinylmalononitriles with nitroolefins in ethanol at reflux. A series of 2-amino-3-nitrobenzonitriles were obtained in reasonable yields. The straightforward and green protocol was found to be fairly efficient, and the catalyst could be recycled and reused in subsequent reactions with consistent activity. The mechanism of the reaction was discussed.
- Chen, Zhiwei,Ding, Kai,Su, Weike
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experimental part
p. 1410 - 1420
(2011/06/11)
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- Synthesis of polyfunctionally substituted thiophene, thieno[2,3-b]pyridine and thieno[2,3-d]pyrimidine derivatives
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The thiophne derivatives 4a-c were prepared according to the Gewald procedure. Their reactivity towards a variety of chemical reagents was studied to give thienopyridines and pyrimidines. Biological investigations were carried on the newly synthesized pro
- Wardakhan, Wagnat W.,Shams, Hoda Z.,Moustafa, Hosam E.
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p. 1815 - 1827
(2007/10/03)
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- Synthesis of substituted 2-iminothiopyrans from aryl ethylidene malononitriles
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The addition of arylethylidene malononitriles 1 to dimethyl trithiocarbonate in the presence of sodium hydride in benzene gives 4-aryl-2-imino-6-methylthio-2H-thiopyran-3-carbonitriles 5 in good yields.
- Samuel,Asokan
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p. 834 - 836
(2007/10/03)
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- SYNTHESIS AND CHEMICAL REACTIVITY OF 4,4-DISUBSTITUTED PYRANAMINES
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The synthesis of a variety of 4,4-disubstituted 4H-pyranamines from alkylarylpropenenitriles and benzoylacetonitrile is reported.The reaction requirements demanded a different approach from the general synthesis of 2-amino-4H-pyrans.Electronic and steric
- Martin-Leon, Nazario,Segura, Jose L.,Seoane, Carlos,Soto, Jose L.
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p. 2434 - 2452
(2007/10/02)
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