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8-Methyl-2-phenylimidazo[1,2-a]pyridine is a chemical compound with the molecular formula C14H11N3. It is a derivative of imidazo[1,2-a]pyridine, which is a heterocyclic aromatic compound. This particular compound features a methyl group at the 8th position and a phenyl group at the 2nd position, which are both substituents that modify the chemical properties and reactivity of the parent imidazo[1,2-a]pyridine structure. It is an organic molecule that can be found in various chemical research and pharmaceutical applications, particularly in the synthesis of potential drug candidates or as a building block in the creation of more complex molecules. The compound's properties, such as solubility, stability, and reactivity, can be influenced by the presence of these substituents, making it a versatile component in organic synthesis.

885-89-2

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885-89-2 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 885-89-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,8 and 5 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 885-89:
(5*8)+(4*8)+(3*5)+(2*8)+(1*9)=112
112 % 10 = 2
So 885-89-2 is a valid CAS Registry Number.

885-89-2Relevant academic research and scientific papers

Micellar Catalysis: Visible-Light Mediated Imidazo[1,2-a]pyridine C—H Amination with N-Aminopyridinium Salt Accelerated by Surfactant in Water

Yang, Zhonglie,Cao, Kun,Peng, Xiaoyan,Lin, Li,Fan, Danchen,Li, Jun-Long,Wang, Jingxia,Zhang, Xiaobin,Jiang, Hezhong,Li, Jiahong

supporting information, p. 3347 - 3352 (2021/10/20)

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

Metal-free, Tf2NH-catalyzed 1, 6-conjugate addition of imidazopyridine to para-quinone methides: Easy access to C3-functionalized triarylmethane imidazopyridine

Khonde, Nilesh S.,Said, Madhukar S.,Sabane, Jagjivan K.,Gajbhiye, Jayant M.,Kumar, Pradeep

supporting information, (2021/10/30)

An inexpensive and commercially available Tf2NH-catalyzed 1,6-conjugate addition of imidazopyridine (IMPY) heterocycles to para-quinone methides (p-QMs) is reported. The present transformation provides a diverse class of C3-functionalized triarylmethanes heterocyclic derivatives of imidazopyridine. These metal-free transformations provided a very broad substrate scope of conjugate addition product with a high yield up to 97% within a short duration.

Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines

Kim, Wansoo,Kim, Hun Young,Oh, Kyungsoo

, p. 15973 - 15991 (2021/07/26)

Oxidation potential-guided electrochemical radical-radical cross-coupling reactions between N-heteroarenes and sodium sulfinates have been established. Thus, simple cyclic voltammetry measurement of substrates predicts the likelihood of successful radical-radical coupling reactions, allowing the simple and direct synthetic access to 3-sulfonylated imidazopyridines and indolizines. The developed electrochemical radical-radical cross-coupling reactions to sulfonylated N-heteroarenes boast the green synthetic nature of the reactions that are oxidant- and metal-free.

Iodine-Mediated Sulfenylation of Imidazo[1,2- a ]pyridines with Ethyl Arylsulfinates

Sun, Jian,Mu, Yangxiu,Iqbal, Zafar,Hou, Jing,Yang, Minghua,Yang, Zhixiang,Tang, Dong

supporting information, p. 1014 - 1018 (2021/03/15)

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.

PhI(OAc)2-mediated oxidative C[sbnd]H sulfoximination of imidazopyridines under mild conditions

Luan, Nannan,Liu, Zhenwei,Han, Shuaijun,Shen, Linhua,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng

supporting information, (2019/11/26)

A facile protocol for direct oxidative C[sbnd]N bond coupling of unactivated imidazo[1,2-a]pyridines with NH-sulfoximines was disclosed using sulfoximines as the nitrogen sources in the presence of (diacetoxy)iodobenzene (PhI(OAc)2). The reacti

Design, one-pot green synthesis and antimicrobial evaluation of novel imidazopyridine bearing pyran bis-heterocycles

Thakur, Ashima,Pereira, Gavin,Patel, Chetananda,Chauhan, Vinita,Dhaked, Ram Kumar,Sharma, Abha

, (2020/01/23)

Herein, we report design, one pot synthesis and antibacterial evaluation of novel imidazopyridine bearing pyran bis-heterocycles. The compounds were synthesized in an aqueous solution of gluconic acid under both conventional heating and ultrasound irradiation. The target compounds were obtained in good to moderate yields with yield of 65–88% in 20–60 min under ultrasonic irradiation. The compounds were characterized by spectroscopic methods IR, 1H NMR, 13C NMR, MS and HRMS. X-ray single crystal structure of 7i was also determined. The compounds were evaluated for antibacterial activity by measuring zone of inhibition using disk diffusion method that revealed that some compounds were inhibiting the growth of Gram +ve and Gram -ve bacteria. Result of minimum inhibitory concentration (MIC) showed that 7a, 7h & 7k from a series 7a-7k inhibited the growth of S. aureus. The minimum bactericidal concentration (MBC) value was determined for 7a, 7h & 7k. MBC/MIC ratio of the derivatives 7a, 7k & 7h suggest former two derivatives act as bactericidal agent & later act as bacteriostatic agents against Gram +ve bacteria. Haemolysis results showed that compounds are non-cytotoxic to erythrocytes.

Unconventional Reactivity with DABCO-Bis(sulfur dioxide): C–H Bond Sulfenylation of Imidazopyridines

Le Bescont, Julie,Breton-Patient, Chloé,Piguel, Sandrine

, p. 2101 - 2109 (2020/04/07)

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.

Metal-Free Regioselective Alkylation of Imidazo[1,2- a ]pyridines with N -Hydroxyphthalimide Esters under Organic Photoredox Catalysis

Jin, Can,Sun, Bin,Xu, Min,Xu, Tengwei,Yang, Jin,Zhang, Liang,Zhu, Rui

supporting information, p. 363 - 368 (2020/02/27)

A visible-light-induced direct C-H alkylation of imidazo[1,2- a ]pyridines has been developed. It proceeds at room temperature by employing inexpensive Eosin Y as a photocatalyst and alkyl N -hydroxyphthalimide (NHP) esters as alkylation reagents. A varie

Multicomponent Synthesis of Imidazo[1,2- a]pyridines: Aerobic Oxidative Formation of C-N and C-S Bonds by Flavin-Iodine-Coupled Organocatalysis

Okai, Hayaki,Tanimoto, Kazumasa,Ohkado, Ryoma,Iida, Hiroki

supporting information, p. 8002 - 8006 (2020/11/02)

Herein, we report an aerobic oxidative C-N bond-forming process that enables the facile synthesis of imidazo[1,2-a]pyridines and takes advantage of a coupled organocatalytic system that uses flavin and iodine. Furthermore, the dual catalytic system can be applied to the one-pot, three-step synthesis of 3-thioimidazo[1,2-a]pyridines from aminopyridines, ketones, and thiols.

Rhodium(II)-Catalyzed Regioselective C3-Alkylation of 2-Arylimidazo[1,2-a]pyridines with Aryl Diazoesters

Kim, Hyunseok,Byeon, Minhyeon,Jeong, Eunchong,Baek, Yonghyeon,Jeong, Seung Jin,Um, Kyusik,Han, Sang Hoon,Han, Gi Uk,Ko, Gi Hoon,Maeng, Chanyoung,Son, Jeong-Yu,Kim, Dongwook,Kim, Sung Hong,Lee, Kooyeon,Lee, Phil Ho

supporting information, p. 2094 - 2106 (2019/03/21)

A regioselective C3-alkylation based on the reaction of 2-arylimidazo[1,2-a]pyridines with a wide range of aryl α-diazoesters in the presence of a Rh(II) catalyst in dichloroethane at room temperature was developed. This method could be applied in the synthesis of benzoimidazoquinolizinone and cycloheptaimidazopyridinone, which are novel heterocyclic scaffolds. (Figure presented.).

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