- Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones
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Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.
- Wang, Ya,Zhou, Yao,Ma, Xingxing,Song, Qiuling
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p. 5599 - 5604
(2021/08/01)
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- Micellar Catalysis: Visible-Light Mediated Imidazo[1,2-a]pyridine C—H Amination with N-Aminopyridinium Salt Accelerated by Surfactant in Water
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A light-promoted metal-free protocol for the amination of imidazo[1,2-a]pyridines with N-aminopyridinium salt by the assistance of surfactants in water was reported, charactering mild and environmentally benign conditions, as well as great functional grou
- Yang, Zhonglie,Cao, Kun,Peng, Xiaoyan,Lin, Li,Fan, Danchen,Li, Jun-Long,Wang, Jingxia,Zhang, Xiaobin,Jiang, Hezhong,Li, Jiahong
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supporting information
p. 3347 - 3352
(2021/10/20)
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- Iodine-Mediated Sulfenylation of Imidazo[1,2- a ]pyridines with Ethyl Arylsulfinates
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A simple iodine-mediated approach is reported for the synthesis of sulfenylated imidazo[1,2- a ]pyridines through the reaction of imidazo[1,2- a ]pyridines with ethyl arylsulfinates under mild conditions. The reaction scope was investigated, and a plausible mechanism is proposed to elucidate the reaction process and activation mode. The results indicate that ethyl sulfinates are efficient sulfur sources for the construction of C-S bonds.
- Sun, Jian,Mu, Yangxiu,Iqbal, Zafar,Hou, Jing,Yang, Minghua,Yang, Zhixiang,Tang, Dong
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supporting information
p. 1014 - 1018
(2021/03/15)
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- Unconventional Reactivity with DABCO-Bis(sulfur dioxide): C–H Bond Sulfenylation of Imidazopyridines
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This work highlights the unexpected and unprecedented outcome of the reactivity with DABCO-bis(sulfur dioxide). The use of this reagent led to the exclusive introduction of a sulfur atom on the C-3 position of imidazopyridines instead of a sulfone group.
- Le Bescont, Julie,Breton-Patient, Chloé,Piguel, Sandrine
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p. 2101 - 2109
(2020/04/07)
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- Electrochemically initiated intermolecular C-N formation/cyclization of ketones with 2-aminopyridines: An efficient method for the synthesis of imidazo[1,2-: A] pyridines
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Electrochemical intermolecular C-N formation/cyclization of ketones with 2-aminopyridines using catalytic hydriodic acid as the redox mediator was developed, providing imidazo[1,2-a]pyridines under more environmentally benign conditions. The reaction proceeds in a simple undivided cell, using low toxic ethanol as the solvent, without external oxidants, and exhibits high atom economy. A variety of ketones including acetophenones, unsatruated and alkyl ketones are amenable to this reaction, affording the corresponding products in moderate to excellent yields. A three-component tandem reaction realizing C-N, C-S/C-Se bond formation can also be achieved under standard conditions.
- Feng, Mei-Lin,Li, Shu-Qi,He, Hui-Zi,Xi, Long-Yi,Chen, Shan-Yong,Yu, Xiao-Qi
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supporting information
p. 1619 - 1624
(2019/04/08)
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- Three Sequential C-N Bond Formations: Tert-Butyl Nitrite as a N1 Synthon in a Three Component Reaction Leading to Imidazo[1,2-a]quinolines and Imidazo[2,1-a]isoquinolines
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tert-Butyl nitrite serves the dual role of an oxidant as well as a N1 synthon in a multicomponent reaction involving quinolines, isoquinolines, and styrenes. Herein, two sp2 C-H functionalizations of styrenes and one sp2 C-H functionalization of quinolines and isoquinolines lead to the formation of fused quinolines and isoquinolines via three sequential C-N bond formations.
- Sau, Prasenjit,Rakshit, Amitava,Modi, Anju,Behera, Ahalya,Patel, Bhisma K.
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p. 1056 - 1064
(2018/01/28)
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- Rapid and efficient one-pot microwave-assisted synthesis of 2-phenylimidazo[1,2-a]pyridines and 2-phenylimidazo[1,2-a]quinoline in water–PEG-400
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An effective, expeditious, environmentally benign one-pot synthesis of 2-phenylimidazo[1,2-a]pyridines and 2-phenylimidazo[1,2-a]quinoline from easily available starting materials as aromatic carbonyl compound, 2-amino pyridine, succinamide, and in situ g
- Jadhav, Santosh A.,Shioorkar, Mahesh G.,Chavan, Omprakash S.,Sarkate, Aniket P.,Shinde, Devanand B.
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p. 285 - 290
(2017/02/10)
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- Ligand-Controlled Synthesis of Azoles via Ir-Catalyzed Reactions of Sulfoxonium Ylides with 2-Amino Heterocycles
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An iridium-catalyzed method was developed for the synthesis of imidazo-fused pyrrolopyrazines. The presence or absence of a nitrogenated ligand controlled the outcome of the reaction, leading to simple β-keto amine products in the absence of added ligand and the cyclized 7- and 8-substituted-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine products in the presence of ligand. This catalyst control was conserved across a variety of ylide and amine coupling partners. The substrate was shown to act as a ligand for the iridium catalyst in the absence of other ligands via NMR spectroscopy. Kinetic studies indicated that formation of the Ir-carbene was reversible and the slow step of the reaction. These mechanistic investigations suggest that the β-keto amine products form via an intramolecular carbene N-H insertion, and the imidazopyrrolopyrazines form via an intermolecular carbene N-H insertion.
- Phelps, Alicia M.,Chan, Vincent S.,Napolitano, José G.,Krabbe, Scott W.,Schomaker, Jennifer M.,Shekhar, Shashank
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p. 4158 - 4169
(2016/06/09)
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- Heteroaromatic imidazo[1,2-a]pyridines synthesis from C-H/N-H oxidative cross-coupling/cyclization
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A novel silver-mediated highly selective C-H/N-H oxidative cross-coupling/cyclization between 2-aminopyridines and terminal alkynes has been demonstrated. This approach provided a simple way to construct heteroaromatic imidazo[1,2-a]pyridines. By using this protocol, the marketed drug zolimidine (antiulcer) could be synthesized easily.
- He, Chuan,Hao, Jing,Xu, Huan,Mo, Yiping,Liu, Huiying,Han, Juanjuan,Lei, Aiwen
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supporting information
p. 11073 - 11075,3
(2012/12/12)
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- Heteroaromatic imidazo[1,2-a]pyridines synthesis from C-H/N-H oxidative cross-coupling/cyclization
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A novel silver-mediated highly selective C-H/N-H oxidative cross-coupling/cyclization between 2-aminopyridines and terminal alkynes has been demonstrated. This approach provided a simple way to construct heteroaromatic imidazo[1,2-a]pyridines. By using this protocol, the marketed drug zolimidine (antiulcer) could be synthesized easily.
- He, Chuan,Hao, Jing,Xu, Huan,Mo, Yiping,Liu, Huiying,Han, Juanjuan,Lei, Aiwen
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supporting information
p. 11073 - 11075
(2013/01/15)
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- REACTION OF α-BROMOACETOPHENONE PHENYLSULFONYLHYDRAZONES. A NEW SYNTHETIC ROUTE TO 2-ARYLIMIDAZOISOQUINOLINES AND -QUINOLINES
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2-Arylimidazoisoquinolines and -quinolines were obtained in good to moderate yields by the reaction of the title hydrazones with isoquinoline and quinoline, respectively.
- Ito, Suketaka,Kakehi, Akikazu,Miwa, Toshikazu
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p. 2373 - 2380
(2007/10/02)
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