- Cobalt-Catalyzed Cross-Dehydrogenative Coupling Reactions of (Benz)oxazoles with Ethers
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The cobalt-catalyzed cross-dehydrogenative coupling of (benz)oxazoles and ethers is described. Access to some important bioactive heteroaryl ether derivatives was achieved using CoCO3 as an inexpensive catalyst at levels as low as 1.0 mol %. In
- Li, Yanrong,Wang, Mengshi,Fan, Wei,Qian, Fen,Li, Guigen,Lu, Hongjian
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- 4-PHENYL-N-(PHENYL)THIAZOL-2-AMINE DERIVATIVES AND RELATED COMPOUNDS AS ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS FOR THE TREATMENT OF E.G. ANGIOGENESIS IMPLICATED OR INFLAMMATORY DISORDERS
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4-phenyl-N-(phenyl)thiazol-2-amine and 4-(pyridin-3-yl)-N-( phenyl) thiazol-2-amine derivatives and the corresponding thiadiazole, thiophene, oxazole, oxadiazole, imidazole and triazole derivatives and related compounds as aryl hydrocarbon receptor (AHR) agonists for the treatment of angiogenesis implicated disorders, such as e.g. retinopathy, psoriasis, rheumatoid arthritis, obesity and cancer, or inflammatory disorders.
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Paragraph 00221; 00242
(2021/06/26)
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- Reaction Conditions for the Regiodivergent Direct Arylations at C2- or C5-Positions of Oxazoles using Phosphine-Free Palladium Catalysts
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Two sets of reaction conditions for the regiodivergent C2- or C5- direct arylations of oxazole are reported. In both cases, phosphine-free catalysts and inexpensive bases were employed allowing the access to the arylated oxazoles in moderate to high yields. Using Pd(OAc)2/KOAc as catalyst and base, regioselective C5-arylations were observed; whereas, using Pd(acac)2/Cs2CO3 system, the arylation occurred at the C2-position of oxazole. The higher reactivity of C5-H bond of oxazole as compared to the C2-H bond in the presence of Pd(OAc)2/KOAc system is consistent with a concerted metalation deprotonation mechanism; whereas the C2-arylation likely occurs via a simple base deprotonation of the oxazole C2-position. Then, from these C2- or C5-arylated oxazoles, a second palladium-catalyzed direct C?H bond arylation affords 2,5-diaryloxazoles with two different aryl groups. We also applied these sequential arylations to the straightforward synthesis of 2-arylphenanthro[9,10-d]oxazoles via three C?H bond functionalization steps. The Ru-catalyzed C?H arylation of the aryl unit of 2-aryloxazoles is also described. (Figure presented.).
- Shi, Xinzhe,Soulé, Jean-Fran?ois,Doucet, Henri
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p. 4748 - 4760
(2019/09/12)
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- Tandem oxidative isocyanide-based cycloaddition reactions in the presence of MIL-101(Cr) as a reusable solid catalyst
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The tandem oxidative three-component synthesis of two types of the heterocycles such as furans and imidazopyridines, via isocyanides [1+4] cycloaddition reactions in the presence of MIL-101(Cr) under aerobic conditions are reported. When the 4-toluenesulfonylmethyl isocyanide was used, an unexpected [3+2] cycloaddition reaction of isocyanides with aldehydes accomplished and dihydrophenyloxazoles and phenyloxazoles produced. These syntheses were successfully carried out using a wide scope of the substrates.
- Shaabani, Ahmad,Sepahvand, Heshmatollah,Amini, Mostafa M.,Hashemzadeh, Alireza,Borjian Boroujeni, Mahmoud,Badali, Elham
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p. 1832 - 1837
(2018/03/07)
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- Tandem cycloaddition-decarboxylation of α-keto acid and isocyanide under oxidant-free conditions towards monosubstituted oxazoles
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An efficient method, tandem [3 + 2] cycloaddition-decarboxylation of α-keto acid and isocyanide promoted by copper salt, has been developed. Under oxidant-free conditions, a series monosubstituted oxazoles have been constructed. Different from the traditional application of α-oxo acids as acyl surrogates, the elegant approach herein ingeniously avoids consuming excess oxidants.
- Zhang, Ling-Juan,Xu, Mei-Chen,Liu, Jie,Zhang, Xian-Ming
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p. 73450 - 73453
(2016/08/18)
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- A One-Pot Tandem Approach for the Synthesis of 5-(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides
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A new modified van Leusen strategy has been developed for the synthesis of biologically significant 5-substituted oxazoles by the reaction of (het)aryl methyl alcohols or benzyl bromides as precursors with tosylmethylisocyanide (TosMIC) under basic conditions. This method is efficient, takes place under mild reaction conditions, and is tolerant of various functional groups with high yield.
- Vinay Kumar, Koravangala S.,Swaroop, Toreshettahally R.,Rajeev, Narasimhamurthy,Vinayaka, Ajjampura C.,Lingaraju, Gejjalagere S.,Rangappa, Kanchugarakoppal S.,Sadashiva, Maralinganadoddi P.
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supporting information
p. 1363 - 1366
(2016/06/01)
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- Nickel-catalyzed decarboxylative acylation of heteroarenes by sp 2 C-H functionalization
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Nickel-catalyzed ligand-free decarboxylative cross-coupling of azole derivatives with α-oxoglyoxylic acids has been developed. This work represents the first example of decarboxylative cross-coupling reactions, in a C-H bond functionalization manner, thro
- Yang, Ke,Zhang, Cheng,Wang, Peng,Zhang, Yan,Ge, Haibo
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supporting information
p. 7241 - 7244
(2014/06/23)
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- Nickel-catalyzed decarboxylative arylation of heteroarenes through sp2 C-H functionalization
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The direct decarboxylative arylation of hetereoarenes with benzoic acids through a nickel-catalyzed sp2 C-H functionalization process was developed. This process provides the first examples of decarboxylative cross-coupling reactions with aroma
- Yang, Ke,Wang, Peng,Zhang, Cheng,Kadi, Adnan A.,Fun, Hoong-Kun,Zhang, Yan,Lu, Hongjian
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supporting information
p. 7586 - 7589
(2015/04/22)
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- Copper-mediated C-H/C-H biaryl coupling of benzoic acid derivatives and 1,3-azoles
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Hot couple: A precious-metal-free copper-mediated intermolecular direct biaryl coupling of benzoic acid derivatives and 1,3-azoles has been developed. The key to success is the installation of an amide-based bidentate coordinating group, which is easily removed and transformed into the parent ester groups after the coupling reaction. Kinetic studies indicate that the rate-limiting step is the aromatic C-H bond cleavage of benzoic acid derivatives. Copyright
- Nishino, Mayuko,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information
p. 4457 - 4461
(2013/05/22)
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- Copper-mediated and copper-catalyzed cross-coupling of indoles and 1,3-azoles: Double C-H activation
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A new bronze age: The described copper-mediated cross-coupling with double C-H activation can provide a convergent access to indole-containing biheteroaryls that are of high interest in pharmaceutical and medicinal chemistry. In this strategy an easily attachable and detachable 2-pyrimidyl directing group is used. Moreover, a variant that is catalytic in copper is achieved by using atmospheric oxygen as an ideal co-oxidant (see scheme). Copyright
- Nishino, Mayuko,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information; experimental part
p. 6993 - 6997
(2012/10/07)
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- Palladium-catalyzed direct arylation of N-heteroarenes with arylsulfonyl hydrazides
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Hydrazides applied: A palladium-catalyzed direct Ci-H arylation of heteroarenes, with arylsulfonyl hydrazides as the arylating reagents, has been developed (see scheme). The reaction is chemoselective, in that arylsulfonyl hydrazides containing halogen substituents can be employed without participation of the halogen substituent in the reaction. The method offers a straightforward approach to a variety of aryl-heteroaryl compounds. Copyright
- Liu, Bo,Li, Jian,Song, Feijie,You, Jingsong
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supporting information; experimental part
p. 10830 - 10833
(2012/09/22)
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- Copper-mediated intermolecular direct biaryl coupling
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Copper-mediated intermolecular direct biaryl coupling of arylazines and azoles via dual C-H bond cleavage proceeds even without palladium catalysts. The reaction system shows the high potential of copper salts in direct C-H arylation chemistry and provides a new approach to biaryl motifs, which are ubiquitous in pharmaceuticals and functional materials.
- Kitahara, Masanori,Umeda, Nobuyoshi,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information; body text
p. 2160 - 2162
(2011/04/23)
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- Cobalt-catalyzed addition of azoles to alkynes
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A ternary catalytic system consisting of a cobalt salt, a diphosphine ligand, and a Grignard reagent promotes syn-addition of an azole C(2)-H bond across an unactivated internal alkyne with high chemo-, regio-, and stereoselectivities under mild conditions. Mechanistic experiments suggest that the reaction involves oxidative addition of the oxazolyl C-H bond to the cobalt center, alkyne insertion into the Co-H bond, and reductive elimination of the resulting diorganocobalt species.
- Ding, Zhenhua,Yoshikai, Naohiko
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supporting information; experimental part
p. 4180 - 4183
(2010/11/19)
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- TRPV1 ANTAGONISTS
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Compounds of formula (I) wherein R1, R2, R4, and W are defined in the description are TRPV 1 antagonists with CNS penetration. Compositions comprising such compounds and methods for treating conditions and disorders using
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Page/Page column 16
(2009/05/28)
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- Heterocyclizations via TosMIC-based multicomponent reactions: A new approach to one-pot facile synthesis of substituted quinoxaline derivatives
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A novel multicomponent reaction involving o-phenylenediamines, aldehydes and p-toluenesulfonylmethyl isocyanide (TosMIC) in the presence of a base leading to the formation of quinoxalines in very good yields is described. Georg Thieme Verlag Stuttgart.
- Neochoritis, Constantinos,Stephanidou-Stephanatou, Julia,Tsoleridis, Constantinos A.
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scheme or table
p. 302 - 305
(2009/06/23)
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- A Mild and convenient synthesis of 4-tosyl-4,5-dihydrooxazoles
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A facile and mild synthesis of 4-tosyl-4,5-dihydrooxazoles is described. The reaction between tosyl methyl isocyanide (TosMIC) and cinnamic or aromatic aldehydes is catalyzed by triethylamine, affording trans-5-styryl- or 5-aryl-4-tosyl-4,5-dihydrooxazole
- Companyo, Xavier,Moyano, Albert,Rios, Ramon
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experimental part
p. 293 - 296
(2010/04/23)
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- Reactions between weinreb amides and 2-magnesiated oxazoles: A simple and efficient preparation of 2-acyl oxazoles
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(Chemical Equation Presented) Treatment of oxazole or 5-aryl oxazoles with i-PrMgCl smoothly generates the corresponding 2-Grignard reagents, which react with Weinreb amides to provide exclusively 2-acyl oxazole products.
- Pippel, Daniel J.,Mapes, Christopher M.,Mani, Neelakandha S.
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p. 5828 - 5831
(2008/02/09)
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- Oxazole synthesis with minimal purification: Synthesis and application of a ROMPgel tosmic reagent
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equations presented The synthesis of ring opening metathesis, polymer-supported Tosmic reagent 1 is described. This reagent was utilized in the conversion of aldehydes to oxazoles in good yields and purities.
- Barrett, Anthony G. M.,Cramp, Susan M.,Hennessy, Alan J.,Procopiou, Panayiotis A.,Roberts, Richard S.
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p. 271 - 273
(2007/10/03)
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- Solution-phase parallel oxazole synthesis with TosMIC
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A quaternary ammonium hydroxide ion exchange resin catalyzes the reaction of p-tolylsulfonylmethyl isocyanide (TosMIC) with aromatic aldehydes to give 5-aryloxazoles. The base and the p-tolylsulfinic acid byproduct are removed by simple filtration, result
- Kulkarni, Bheemashankar A.,Ganesan
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p. 5637 - 5638
(2007/10/03)
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- Synthesis and reactivities of 1-(isocyanomethyloxy)benzotriazole as a new source of isocyanomethyl synthon
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The title compound, 1-(isocyanomethyloxy)benzotriazole (6) as a new source of isocyanomethyl synthon, was synthesized in 65% yield by the dehydration of 1-(formamidomethyloxy)benzotriazole with phosphorus oxychloride in the presence of triethylamine. Unde
- Sasaki, Hideaki
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p. 1369 - 1371
(2007/10/03)
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- Synthesis of 2,5-Disubstituted Oxazoles from Aldehydes and N-(Tosylmethyl)imino Synthons. Application to the Synthesis of Pimprinine Analogues
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A series of N-(tosylmethyl)imino compounds has been applied to a new base induced, one-operational synthesis of 2,5-disubstituted oxazoles from aromatic aldehydes.For substituent A of the imino compounds, which becomes the 2-substituent in the oxazoles, has been chosen methoxy, methyl and phenyl.The new method has been used also to synthesize seven pimprinine analogues, i.e., 5-(3-indolyl)oxazoles.
- Houwing, Hendrik A.,Wildeman, Jurjen,van Leusen, Albert M.
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p. 1133 - 1139
(2007/10/02)
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