- Iodopyridines from bromo- and chloropyridines
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Bromo- and chloropyridines may be converted to the corresponding iodopyridines by treatment with sodium iodide and acetyl chloride in acetonitrile.
- Corcoran,Bang
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Read Online
- The Diverse One-Pot Reactions of 2-Quinolylzincates: Homologation, Electrophilic Trapping, Hydroxylation, and Arylation Reactions
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2-Quinolylzincates were efficiently produced from the regioselective metalation reactions of quinoline with various organozincates as key intermediates. The four different types of title reactions of these intermediates under the presented reaction conditions allowed for the facile formation of the corresponding C-2 functionalized quinolines, which are not successfully accessed through typical zincation methods.
- Jeong, Hye Jin,Chae, Suyeon,Jeong, Keunhong,Namgoong, Sung Keon
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supporting information
p. 6343 - 6349
(2018/10/31)
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- Probing the catalytic promiscuity of a regio- and stereospecific C-glycosyltransferase from Mangifera indica
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The catalytic promiscuity of the novel benzophenone C-glycosyltransferase, MiCGT, which is involved in the biosynthesis of mangiferin from Mangifera indica, was explored. MiCGT exhibited a robust capability to regio- and stereospecific C-glycosylation of 35 structurally diverse druglike scaffolds and simple phenolics with UDP-glucose, and also formed O- and N-glycosides. Moreover, MiCGT was able to generate C-xylosides with UDP-xylose. The OGT-reversibility of MiCGT was also exploited to generate C-glucosides with simple sugar donor. Three aryl-C-glycosides exhibited potent SGLT2 inhibitory activities with IC50 values of 2.6×, 7.6×, and 7.6×10-7-M, respectively. These findings demonstrate for the first time the significant potential of an enzymatic approach to diversification through C-glycosidation of bioactive natural and unnatural products in drug discovery. C-glycodiversification: MiCGT, as the first benzophenone C-glycosyltransferase (CGT) from Mangifera indica, showed robust regio- and stereospecific C-glycosylation activity for 35 structurally diverse acceptors with UDP-glucose or xylose. The aryl-C-glycoside 1 exhibited potent antidiabetic activity toward SGLT2.
- Chen, Dawei,Chen, Ridao,Wang, Ruishan,Li, Jianhua,Xie, Kebo,Bian, Chuancai,Sun, Lili,Zhang, Xiaolin,Liu, Jimei,Yang, Lin,Ye, Fei,Yu, Xiaoming,Dai, Jungui
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supporting information
p. 12678 - 12682
(2015/10/28)
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- Synthesis of 7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) via Pd-catalyzed directed double C-H functionalization of 8,8′-biquinolyl: Emergence of an atropos from a tropos state
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7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) was prepared from 2-chloroaniline in four steps: (1) the Skraup reaction, (2) Ni-catalyzed reductive coupling of 8-chloroquinoline, (3) Pd(II)-catalyzed double C-H functionalization of 8,8′-biquinolyl mediated by
- Wang, Chao,Flanigan, Darrin M.,Zakharov, Lev N.,Blakemore, Paul R.
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scheme or table
p. 4024 - 4027
(2011/10/02)
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- AMINO-HETEROCYCLIC COMPOUNDS
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The invention provides PDE9-inhibiting compounds of Formula (I), and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, A, and n are as defined herein. Pharmaceutical compositions containing the compounds of Formula I, and uses thereof in treating neurodegenerative and cognitive disorders, such as Alzheimer's disease and schizophrenia, are also provided.
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Page/Page column 22
(2010/08/07)
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- One-pot iodination of hydroxypyridines
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(Chemical Equation Presented) A one-pot, high-yielding iodination of hydroxypyridines and hydroxyquinolines is described. The iodination proceeds under mild conditions, and the products are obtained in high yield without the need for chromatographic purif
- Maloney, Kevin M.,Nwakpuda, Emily,Kuethe, Jeffrey T.,Yin, Jingjun
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supporting information; experimental part
p. 5111 - 5114
(2009/10/24)
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- Microwave-assisted trans-halogenation reactions of various chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines, isoquinolines, and pyridines leading to the corresponding iodinated heterocycles
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(Chemical Equation Presented) Microwave irradiation of certain chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines in the presence of acetic anhydride and sodium iodide leads, via a trans-halogenation process, to the corresponding iodides in high yield. Related conversions involving pyridines and isoquinolines can also be achieved under similar conditions.
- Bissember, Alex C.,Banwell, Martin G.
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supporting information; experimental part
p. 4893 - 4895
(2009/10/02)
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- Aryl pyrrolidinyl and piperidinyl ketone derivatives and uses thereof
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Aryl and heteroaryl ketone compounds substituted with pyrrolidines and piperidines, that modulate serotonin norepinephrine and/or dopamine neurotransmission. Also provided are pharmaceutical compositions, methods of using, and methods of preparing the com
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Page/Page column 44-45
(2009/12/28)
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- Heteroaryl pyrrolidinyl and piperidinyl ketone derivatives and uses thereof
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Compounds of the formula: or pharmaceutically acceptable salts thereof, wherein m, n, Ar, R1, R2, Ra and Rb are defined herein. Also provided are pharmaceutical compositions, methods of using, and methods of pre
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Page/Page column 118
(2008/12/06)
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- Tributylmagnesium ate complex-mediated bromine-magnesium exchange of bromoquinolines: A convenient access to functionalized quinolines
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2-, 3- and 4-bromoquinolines were converted to the corresponding lithium tri(quinolyl)magnesates at -10°C by treatment with Bu3MgLi in THF or toluene. The resulting organomagnesium derivatives were quenched by various electrophiles to afford functionalized quinolines.
- Dumouchel, Sylvain,Mongin, Florence,Trécourt, Fran?ois,Quéguiner, Guy
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p. 2033 - 2035
(2007/10/03)
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- Silyl-mediated halogen/halogen displacement in pyridines and other heterocycles
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Heating with bromotrimethylsilane converts 2-chloropyridine into 2-bromopyridine and 2-chloro-6-methylpyridine into 2-bromo-6-methylpyridine. Both 2-chloropyridines and 2-bromopyridines give the corresponding iodo compound when treated with in situ generated iodotrimethylsilane. Although 3- and 4-chloropyridine are completely inert, 2,4-dichloropyridine undergoes the halogen/halogen exchange simultaneously at the 2- and 4-position. Halogen displacement takes place exclusively at the 2-position with 2,3-dichloropyridine and 2,5-dichloropyridine. In agreement with the intermediacy of N-trimethylsilylpyridinium salts as a prerequisite for the occurrence of halogen exchange, neither 2-fluoropyridine and 2-fluoro-6-methylpyridine nor any 2,6-dihalopyridine reacts. Finally, bromine/chlorine and iodine/chlorine substitution can also be accomplished with 2-or 4-chloroquinoline, 1-chloroisoquinoline, 2-chloropyrimidine, chloropyrazine and 2,3-dichloroquinoxaline as substrates. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).
- Schlosser, Manfred,Cottet, Fabrice
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p. 4181 - 4184
(2007/10/03)
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- Application of phosphonium salts to the reactions of various kinds of amides
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The phosphonium salts 1 and 2 prepared from triphenylphosphine and N-halogenosuccinimide proved to be applicable to the conversion of amide compounds. Especially, halogenation of electron-deficient heteroaromatic alcohols with these reagents seems to be a convenient method compared to the halogenation with phosphorus oxyhalides.
- Sugimoto, Osamu,Mori, Miho,Moriya, Keisuke,Tanji, Ken-Ichi
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p. 1112 - 1118
(2007/10/03)
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- Studies on Organometallic Compounds. II. Facile and Convenient Method for the Synthesis of Idoazines through Iododestannation of Trimethylstannylazines
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Trimethylsatannyl and bis(trimethylstannyl) derivatives of pyridine, quinoline, and isoquinoline were prepared from the corresponding halo and dihalo (chloro or bromo) derivatives and trimethylstannyl sodium, which was generated in situ from chlorotrimethylsatannane and sodium.These stannyl derivatives readily underwent iododestannation on treatment with iodine to produce the corresponding iodo and diiodo derivatives of pyridine, quinoline, and isoquinoline, respectively, in good yields.Keywords -trimethylsannylazine; bis(trimethylstannyl)azine; iodoazine; diiodoazine; iododestannation; trimethylstannyl sodium; chlorotrimethylstannane
- Yamamoto, Yukata,Yanagi, Akihiko
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p. 1731 - 1737
(2007/10/02)
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