- Regioselective synthesis of nitrosoimidazoheterocycles using tert-butyl nitrite
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A simple and practical method has been developed for the regioselective nitrosylation of imidazopyridines via C(sp2)-H bond functionalization using tert-butyl nitrite under mild reaction conditions in a short time. A library of 3-nitrosoimidazo
- Monir, Kamarul,Ghosh, Monoranjan,Jana, Sourav,Mondal, Pallab,Majee, Adinath,Hajra, Alakananda
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- Ring-ring interconversions of nitrosoimidazoles. The effect of some condensed six-membered rings on the reactivity
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The study of the effect of a condensed ring on the reactivity of nitrosoimidazoles with hydrochloric acid has been extended to some six-membered rings: thus, the reactivity of 2-(4-chlorophenyl)-3-nitrosoimidazo[1,2-a]pyridine (6), 6-chloro-2-(4-chlorophenyl)-3-nitrosoimidazo[1,2-b]pyridazine (7), 2-(4-chlorophenyl)-3-nitrosoimidazo[1,2-a]pyrimidine (8a) and 2-(4-chlorophenyl)-3-nitrosoimidazo[1,2-a]pyrazine (9) has been examined. The striking differences observed in the reactivity of compounds 6-9 (denitrosation, ring-opening with ammonia elimination, ring-ring interconversion with the unexpected loss of a C3 fragment and decomposition, respectively) have been discussed. (C) 2000 Elsevier Science Ltd.
- Billi,Cosimelli,Spinelli,Andreani,Leoni
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- Difluorinative-hydroxylation and C-3 functionalization (halogenation/SCN/NO) of imidazopyridine using Selectfluor as fluorine source or oxidant respectively
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An efficient route for the difluorinative-hydroxylation through dearomative difunctionalization of imidazopyridine using Selectfluor as fluorine source has been developed in an aqueous medium. The reaction proceeds through ionic followed by radical pathwa
- Balasubramanian, Sridhar,Kalari, Saradhi,Rode, Haridas B.
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supporting information
(2021/04/15)
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- Catalyst-Free Regioselective C-3 Nitrosation of Imidazopyridines with tert -Butyl Nitrite under Neutral Conditions
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We have successfully developed a novel and efficient catalyst-free method for the synthesis of 3-nitroso-substituted imidazopyridines, from readily available imidazo[1,2-a]pyridines and tert-butyl nitrite, in good to excellent yields. Importantly, the use
- Yang, Daoshan,Yan, Kelu,Wei, Wei,Liu, Yao,Zhang, Mengqi,Zhao, Caixia,Tian, Laijin,Wang, Hua
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p. 122 - 130
(2015/12/26)
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- NaNO2/I2-Mediated Regioselective Synthesis of Nitrosoimidazoheterocycles from Acetophenones by a Domino Process
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A regioselective synthesis of nitrosoimidazoheterocycles from the reaction of 2-aminopyridines and acetophenones in the presence of NaNO2and I2is described. The reaction is suggested to proceed by a domino process involving sequentia
- Mukhopadhyay, Sushobhan,Dighe, Shashikant U.,Kolle, Shivalinga,Shukla, Praveen K.,Batra, Sanjay
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p. 3836 - 3844
(2016/08/16)
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- Anti-anxiety and sedative profile evaluation of imidazo[1,2-a]pyridine derivatives
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(Table Presented) Three imidazo[1,2-a]pyridine-3-nitrosated (L-1, L-2, L-3) and a 3-formyl imidazo[1,2-a]-pyridine thiosemicarbazone (L-4) were synthesized and evaluated for their effects in the elevated plus maze, burying behavior test, rotarod performance, the horizontal wire test, and locomotor activity. L-2 and L-3 increased the percent time spent in the open arms of the plus maze at doses of 1 and 2 mg/kg without modifying the number of total entries. In addition, L-2 and L-3 (1 mg/kg) increased the number of open arm entries indicating anxiolytic-like activity at this dose. In the burying behavioral test, L-1 (2-8mg/kg), L-2 (8mg/kg), and L-3 (4 and 8mg/kg), induced a clear reduction in cumulative burying behavior, without modifying burying behavior latency, thus reducing experimental anxiety. In the rotarod test, L-1 and L-2 impaired rotarod performance only at the highest evaluated dose (64mg/kg) at which reduction of motor activity was observed and thereby no conclusions about myorelaxant effects can be proposed. All compounds showed a clear sedative effect and corresponding ED50 values were obtained. Results indicate that compounds L-1, L-2, and L-3 show a sedative and an anxiolytic profile.
- Lopez-Martinez, Margarita,Salgado-Zamora, Hector,San-Juan, Eduardo Ramirez,Zamudio, Sergio,Picazo, Ofir,Campos, Maria Elena,Naranjo-Rodriguez, Elia B.
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experimental part
p. 371 - 381
(2012/01/11)
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- Influence of the 2-aryl group on the ipso electrophilic substitution process of 2-arylimidazo[1,2-a]pyridines
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A systematic study of electrophilic substitution reactions of 3-nitroso-2-arylimidazo[1,2-a]pyridine confirmed that the nitroso group may be ipso-substituted by bromine (NBS in DMF) and that bromine in turn may be substituted by the nitroso group. Electro
- Salgado-Zamora, Hector,Velazquez, Manuel,Mejia, Daniel,Campos-Aldrete,Jimenez, Rogelio,Cervantes, Humberto
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