7008-64-2Relevant academic research and scientific papers
CuCl2-catalyzed N[sbnd]O bond cleavage of oxime esters: Approach to imidazoheterocycles and furo[3,2-c]chromenyl fused imidazoles
Gudimella, Santosh K.,Kaur, Amanpreet,Kumar, Ram,Samanta, Sampak
, (2020/07/08)
An articulate approach to a diverse set of imidazoheterocycles in good to high yields via a copper-catalyzed aza-annulation of several oxime esters with a group of 2-amino-azaarenes was developed. The above cyclization reaction probably proceeds via a single electron transfer process which embodies a new technique for creating two new C[sbnd]N bonds for imidazole ring synthesis. Gratifyingly, the implementation of this chemistry could be further stretched to the synthesis of a novel class of fused imidazoles bearing a furo[3,2-c]chromene moiety via a sequential C[sbnd]N bond formation, followed by C(sp2)-H functionalization/5-endo-dig-oxacyclization (C[sbnd]C and C[sbnd]O bonds) of in situ produced fused imidazoles with cyclic enynones in the presence of copper(II) as a π-electrophilic Lewis acid catalyst.
Sodium Salts (NaI/NaBr/NaCl) for the Halogenation of Imidazo-Fused Heterocycles
Semwal, Rashmi,Ravi, Chitrakar,Kumar, Rahul,Meena, Ramavatar,Adimurthy, Subbarayappa
, p. 792 - 805 (2019/01/24)
We report herein an effective method for the halogenation of imidazo-fused heterocycles using readily available sodium salts (NaCl/NaBr/NaI) as halogen source and K2S2O8 (or) oxone as promoter. A variety of C-3 halogenated imidazo[1,2-a]pyridines and benzo[d]imidazo[2,1-b]thiazoles were obtained in good to excellent yields. The present method of halogenation has been also extended to 2-aminopyridines, 2-aminopyrimidine, indole, and isoquinoline with moderate to excellent yields.
DL5050, a Selective Agonist for the Human Constitutive Androstane Receptor
Liang, Dongdong,Li, Linhao,Lynch, Caitlin,Diethelm-Varela, Benjamin,Xia, Menghang,Xue, Fengtian,Wang, Hongbing
supporting information, p. 1039 - 1044 (2019/07/03)
The constitutive androstane receptor (CAR) is a xenobiotic sensor governing the transcription of genes involved in drug disposition, energy homeostasis, and cell proliferation. However, currently available human CAR (hCAR) agonists are nonselective, which
Human constitutive androstane receptor agonist DL5016: A novel sensitizer for cyclophosphamide-based chemotherapies
Liang, Dongdong,Li, Linhao,Lynch, Caitlin,Mackowiak, Bryan,Hedrich, William D.,Ai, Yong,Yin, Yue,Heyward, Scott,Xia, Menghang,Wang, Hongbing,Xue, Fengtian
, p. 84 - 99 (2019/06/27)
The DNA alkylating prodrug cyclophosphamide (CPA), alone or in combination with other agents, is one of the most commonly used anti-cancer agents. As a prodrug, CPA is activated by cytochrome P450 2B6 (CYP2B6), which is transcriptionally regulated by the
A copper-catalyzed multi-component reaction accessing fused imidazo-heterocycles via C-H functionalization
Kumar, G. Santosh,Ragini, S. Pushpa,Kumar, A. Sanjeeva,Meshram
, p. 51576 - 51580 (2015/06/25)
An efficient synthesis of fused imidazo-heterocycles is described using Cu(OTf)2 in [bmim]BF4 by the multi-component reaction of pyridin-2(1H)-one or thiazol/benzo[d]thiazol-2(3H)-ones with O-tosylhydroxyl amine and acetophenones under microwave irradiation. The present method is very rapid and the product formation occurs via a C-H functionalization/tandem addition-cyclization process. The ionic liquid containing copper triflate is recovered and reused four times.
Microwave assisted synthesis of novel imidazo [2,1-b]thiazole derivative attached to quinoxalinones
Mukherjee, Chandrani,Watanabe, Kenneth T.,Biehl, Edward R.
, p. 6008 - 6014 (2012/11/07)
3-(6-Phenylimidazo[2,1-b]thiazol-5-yl)quinoxalin-2(1H)-ones (qunoxalinone) (6a-q) have been synthesized by the reaction of ethyl 2-oxo-2-(6- phenylimidazo[2,1-b]thiazol-5-yl)acetates (4a-e) with suitably substituted o-phenylenediamines (5a-f) under microw
Microwave-assisted Hantzsch thiazole synthesis of N-phenyl-4-(6- phenylimidazo[2,1-b]thiazol-5-yl)thiazol-2-amines from the reaction of 2-chloro-1-(6-phenylimidazo[2,1-b]thiazol-5-yl)ethanones and thioureas
Kamila, Sukanta,Mendoza, Kimberly,Biehl, Edward R.
, p. 4921 - 4924,4 (2020/07/30)
N-Phenyl-4-(6-phenylimidazo[2,1-b]thiazol-5-yl)thiazol-2-amines (6a-q) have been synthesized by the Hantzsch thiazole reaction of 2-chloro-1-(6- phenylimidazo[2,1-b]thiazol-5-yl)ethanones (4a-e) with suitably substituted thioureas using microwave heating.
Hypervalent iodine(iii) sulfonate mediated synthesis of 6-arylimidazo[2,1-b]thiazoles in liquid PEG-400
Wu, Fang-Wen,Hou, Rei-Sheu,Wang, Huey-Min,Kang, Iou-Jiun,Chen, Ling-Ching
experimental part, p. 663 - 666 (2012/07/03)
PEG-400[poly(ethylene glycol-400)] is used as reaction medium in the one-pot synthesis of 6-arylimidazo[ 2,1-b]thiazoles by reaction with aryl ketones, hypervalent iodine(III) sulfonate and 2-aminothiazole. Significant rate enhancements and improved yield
Hypervalent iodine in the synthesis of bridgehead heterocycles: A facile route to the synthesis of 6-arylimidazo[2,1-b]thiazoles using [hydroxy(tosyloxy)iodo]benzene
Aggarwal, Ranjana,Sumran, Garima
, p. 875 - 879 (2007/10/03)
α-Tosyloxyketones (2), readily accessible through hypervalent iodine oxidation of enolizable ketones (1) using [hydroxy(tosyloxy)iodo]benzene (HTIB) in acetonitrile, exclusively generates the 6-arylimidazo[2,1-b]thiazoles (4) on treatment with commerciall
