- Divergent, Enantioselective Synthesis of Pyrroles, 3H-Pyrroles and Bicyclic Imidazolines by Ag- or P-Catalyzed [3+2] Cycloaddition of Allenoates with Activated Isocyanides
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The divergent, stereoselective formal [3+2] cycloadditions of allenoates with activated isocyanides catalyzed by silver or phosphine-based catalysts were investigated. Silver catalysis is capable of delivering a range of 3H-pyrroles in high stereoselectivities. These enantioenriched heterocycles can either undergo sequential cyclisation with isocyanoacetates to deliver unprecedented bicyclic imidazolines with excellent yields and stereoselectivity or undergo unusual aromatization pathways leading to polysubstituted pyrroles. On the other hand, a simple mix-and-go procedure using an amino acid-derived phosphine as the catalyst produces pyrroles bearing a benzylic stereocenter with good enantioselectivity.
- Kok, Germaine Pui Yann,Shao, Pan-Lin,Liao, Jia-Yu,Ismail, Siti Nur Fairuz Bte Sheikh,Yao, Weijun,Lu, Yixin,Zhao, Yu
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- Transformations of alkyl 2-(2,2-disubstituted-ethenyl)amino-3- dimethylaminoprop-2-enoates: Synthesis of alkyl 3,4-disubstituted- and alkyl 1-acyl-3,4-disubstituted pyrrole-2-carboxylates
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Alkyl 3,4-disubstituted pyrrole-2-carboxylates were obtained by cyclization of alkyl-2(2,2-disubstituted-ethenyl)amino-3- (dimethylamino)prop-2-enoates in acidic media, while in the presence of acyl chlorides alkyl 1-acyl-3,4-disubstituted pyrrol-2-carbox
- Selic, Lovro,Stanovnik, Branko
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- Synthesis of carbon-11-labeled 4-(phenylamino)-pyrrolo[2,1-f][1,2,4] triazine derivatives as new potential PET tracers for imaging of p38α mitogen-activated protein kinase
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The reference standards methyl 4-(2-methyl-5-(methoxycarbamoyl)phenylamino) -5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (10a), methyl 4-(2-methyl-5-(ethoxycarbamoyl)phenylamino)-5-methylpyrrolo[2,1-f][1,2,4] triazine-6-carboxylate (10b) and corre
- Wang, Min,Gao, Mingzhang,Zheng, Qi-Huang
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p. 3700 - 3705
(2014/09/17)
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- Pyrrolotriazine inhibitors of kinases
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The present invention provides compounds of formula I and pharmaceutically acceptable salts thereof. The formula I compounds inhibit the tyrosine kinase activity of growth factor receptors such as VEGFR-2, FGFR-1, PDGFR, HER-1, HER-2, thereby making them useful as anti-cancer agents. The formula I compounds are also useful for the treatment of other diseases associated with signal transduction pathways operating through growth factor receptors.
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Page/Page column 33
(2008/06/13)
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- Synthesis and SAR of 4-(3-hydroxyphenylamino)pyrrolo[2,1-f][1,2,4]triazine based VEGFR-2 kinase inhibitors
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A versatile synthesis of the suitably functionalized pyrrolo[2,1-f][1,2,4] triazine nucleus is described. SAR at the C-5 and C-6 positions of the 4-(3-hydroxy-4-methylphenylamino)pyrrolo[2,1-f][1,2,4]triazine template led to compounds with good in vitro potency against VEGFR-2 kinase. Glucuronidation of the phenol group is mitigated by incorporation of a basic amino group on the C-6 side chain of the pyrrolotriazine nucleus.
- Borzilleri, Robert M.,Cai, Zhen-Wei,Ellis, Christopher,Fargnoli, Joseph,Fura, Aberra,Gerhardt, Tracy,Goyal, Bindu,Hunt, John T.,Mortillo, Steven,Qian, Ligang,Tokarski, John,Vyas, Viral,Wautlet, Barri,Zheng, Xioping,Bhide, Rajeev S.
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p. 1429 - 1433
(2007/10/03)
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- Methods of treating p38 kinase-associated conditions and pyrrolotriazine compounds useful as kinase inhibitors
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Methods of treating one or more conditions associated with p38 kinase activity are disclosed comprising administering to a patient in need thereof at least one compound having the formula (I): 1or a pharmaceutically acceptable salt, prodrug, or solvate thereof, wherein R3 is hydrogen, methyl, perfluoromethyl, methoxy, halogen, cyano, or NH2, preferably methyl, and X, R1 through R6, and Z are as described in the specification. Advantageously the groups —ZR4R5 taken together comprise an —NH-substituted aryl.
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