cas 1011-51-4, 5-(4-METHOXYPHENYL)OXAZOLE | Articles data

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Structure-Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells
Targeted therapies for ER+/PR+ and HER2-amplified breast cancers have improved patient survival, but there are no therapies for triple negative breast cancers (TNBC) that lack expression of estrogen and progesterone receptors (ER/PR), or amplification or
Robles, Andrew J.,McCowen, Shelby,Cai, Shengxin,Glassman, Michaels,Ruiz, Francisco,Cichewicz, Robert H.,McHardy, Stanton F.,Mooberry, Susan L.
p. 9275 - 9289
(2017)
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Synthesis, characterization, and antimicrobial evaluation of oxadiazole congeners
A series of 1,3-oxazole, 1,3-thiazole, isomeric 1,2,4-oxadiazole, 1,3,4-oxadiazole, and 1,2,3,4-tetrazole heterocycles was synthesized. All the compounds shared as a common feature the presence of a 4-hydroxyphenyl substituent. The structures of the synthesized compounds were confirmed by MS, 1H-NMR, and elemental analysis. In vitro antimicrobial activity for all the newly synthesized compounds at concentrations of 200-25 μg/mL was evaluated against Gram+ve organisms such as methicillin-resistant Staphylococcus aureus (MRSA), Gram-ve organisms such as Escherichia coli (E. coli), and the fungal strain Aspergillus niger (A. niger) by the cup plate method. Ofloxacin and ketoconazole (10 μg/mL) were used as reference standards for antibacterial and antifungal activity, respectively. Compounds 15, 16, and 20 showed notable antibacterial and antifungal activities at higher concentrations (200 μg/mL), whereas 17-19 were found to display significant antibacterial or antifungal activity (25-50 μg/mL) against the Gram+ve, Gram-ve bacteria, or fungal cells used in the present study.
Sadek, Bassem,Fahelelbom, Khairi Mustafa Salem
p. 4339 - 4347
(2011)
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Reaction Conditions for the Regiodivergent Direct Arylations at C2- or C5-Positions of Oxazoles using Phosphine-Free Palladium Catalysts
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
p. 4748 - 4760
(2019/09/12)

Tosylmethylisocyanide (TosMIC) [3+2] cycloaddition reactions: A facile Van Leusen protocol for the synthesis of the new class of spirooxazolines, spiropyrrolines and Chromeno[3,4-c]pyrrols
The reactivity and chemo-, regio- and diastreo-selectivity of tosylmethyl isocyanides (TosMIC) are investigated in Van Leusen type [3 + 2] cycloaddition reactions with the various activate cyclic ketones and double C–C bonds in the synthesis of spirooxazolines, spiropyrrolines and chromeno[3,4-c]pyrrols in good to excellent yields under catalyst-free conditions without any activation at ambient temperature.
Shaabani, Ahmad,Sepahvand, Heshmatollah,Bazgir, Ayoob,Khavasi, Hamid Reza
p. 7058 - 7067
(2018/11/02)

Improvement of the Van Leusen reaction in the presence of β-cyclodextrin: A green and efficient synthesis of oxazoles in water
An efficient approach for the synthesis of oxazoles through the Van Leusen reaction in the presence of β-cyclodextrin is described. In aqueous medium using β-cyclodextrin as a supramolecular catalyst, tosylmethyl isocyanide was deprotonated by triethylami
Rahimzadeh, Golnaz,Kianmehr, Ebrahim,Mahdavi, Mohammad
p. 923 - 926
(2017/12/18)

An efficient two-step synthesis of 2,5-disubstituted oxazole derivatives involving cu-promoted carbon-carbon single bond formation
Environment sensitive fluorescence probe to detect various organelles is emerging as an excellent tool to attract the attention of a large number of researchers around the globe. The recent developments have shown that oxazole dyes are very competent and can exhibit a useful fluorescence property in this direction. An efficient synthetic procedure towards 2,5-diaryl substituted oxazole derivatives have been reported. It is a two-step technique involving classical van Leusen protocol followed by copper-mediated coupling with aryl halides to introduce the required carbon-carbon single bond. The aryl groups are chosen in such a way so that the aryl functionalities at 2- and 5-positions of oxazole can act as acceptor and donor moiety respectively. Thus, in turn, the extended conjugation from donor moiety to acceptor moiety via the oxazole ring is set up therein. The oxazole derivatives were characterized by various spectroscopic measurements like NMR, IR and MS.
Maiti, Jyotirmay,Biswas, Suman,Das, Ranjan
p. 1519 - 1522
(2016/05/09)

Tandem cycloaddition-decarboxylation of α-keto acid and isocyanide under oxidant-free conditions towards monosubstituted oxazoles
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
p. 73450 - 73453
(2016/08/18)

A One-Pot Tandem Approach for the Synthesis of 5-(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides
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.
supporting information
p. 1363 - 1366
(2016/06/01)

Synthesis and biological activity of 5-(4-methoxyphenyl)-oxazole derivatives
5-(4′-Methoxyphenyl)-oxazole (MPO), originally reported as a synthetic compound, was isolated from fungal culture broth as an inhibitor of hatch and growth of Caenorhabditis elegans. Nineteen MPO derivatives were chemically synthesized, but showed no effect on C. elegans hatch and growth. These findings strongly suggested that the whole structure of MPO is essential for anti-C. elegans activity.
Yamamuro, Daisuke,Uchida, Ryuji,Ohtawa, Masaki,Arima, Shiho,Futamura, Yushi,Katane, Masumi,Homma, Hiroshi,Nagamitsu, Tohru,Osada, Hiroyuki,Tomoda, Hiroshi
supporting information
p. 313 - 316
(2015/04/13)

Cobalt-Catalyzed Decarboxylative 2-Benzoylation of Oxazoles and Thiazoles with α-Oxocarboxylic Acids
Cobalt-catalyzed decarboxylative cross-coupling of oxazoles and thiazoles with α-oxocarboxylic acids was developed through an sp2 C-H bond functionalization process. This work represents the first example of cobalt-catalyzed decarboxylative C-H
Yang, Ke,Chen, Xinyong,Wang, Yuqi,Li, Wanqing,Kadi, Adnan A.,Fun, Hoong-Kun,Sun, Hao,Zhang, Yan,Li, Guigen,Lu, Hongjian
p. 11065 - 11072
(2015/11/18)

Nickel-catalyzed decarboxylative acylation of heteroarenes by sp 2 C-H functionalization
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
supporting information
p. 7241 - 7244
(2014/06/23)

Nickel-catalyzed decarboxylative arylation of heteroarenes through sp2 C-H functionalization
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
supporting information
p. 7586 - 7589
(2015/04/22)

Copper-mediated C-H/C-H biaryl coupling of benzoic acid derivatives and 1,3-azoles
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
supporting information
p. 4457 - 4461
(2013/05/22)

Synthesis and evaluation of photophysical properties of Series of π-conjugated oxazole dyes
Incorporation of π-conjugated spacers at the 2 or 5 position of a 2,5-disubstitutedaryloxazole led to new series of fluorescent dyes. They show emissions from visible to 700 nm along with significant Stokes shift up to 208 nm and a strong solvatochromic fluorescence. These compounds are easily accessible in one step through direct C-H bond functionalization.
Mahuteau-Betzer, Florence,Piguel, Sandrine
supporting information
p. 3188 - 3193
(2013/06/27)

Copper-mediated dehydrogenative biaryl coupling of naphthylamines and 1,3-azoles
A copper-mediated dehydrogenative biaryl cross-coupling of naphthylamines and 1,3-azoles has been developed. The key to its success is the introduction of N,N-bidentate coordination system based on the picolinamide directing group. The reaction proceeds s
Odani, Riko,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
p. 11045 - 11052
(2013/11/19)

Mild palladium-catalyzed regioselective direct arylation of azoles promoted by tetrabutylammonium acetate
A mild, general, and convenient palladium-catalyzed direct arylation of the 5-position of azoles with aryl bromides, efficiently promoted by tetrabutylammonium acetate, is described. 1-Methylpyrazole, oxazole, and thiazole reacted at 70°C in N,N-dimethyla
Bellina, Fabio,Lessi, Marco,Manzini, Chiara
p. 5621 - 5630
(2013/09/12)

Copper-mediated and copper-catalyzed cross-coupling of indoles and 1,3-azoles: Double C-H activation
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
supporting information; experimental part
p. 6993 - 6997
(2012/10/07)

Copper-mediated intermolecular direct biaryl coupling
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
supporting information; body text
p. 2160 - 2162
(2011/04/23)

Highly regioselective palladium-catalyzed direct arylation of oxazole at C-2 or C-5 with aryl bromides, chlorides, and triflates
Complementary palladium-catalyzed methods for direct arylation of oxazole with high regioselectivity (>100:1) at both C-5 and C-2 have been developed for a wide range of aryl and heteroaryl bromides, chlorides, iodides, and triflates. C-5 arylation is pre
Strotman, Neil A.,Chobanian, Harry R.,Guo, Yan,He, Jiafang,Wilson, Jonathan E.
supporting information; experimental part
p. 3578 - 3581
(2010/11/04)

Nickel-catalyzed direct C-H arylation and alkenylation of heteroarenes with organosilicon reagents
"Chemical Equation Presented" Breaking the Si-lence: The direct crosscoupling of heteroarenes with aryl- or alkenylsilanes proceeds efficiently, in the presence of a nickel catalyst, to create a wide range of aryl- and alkenyl-heteroaryl bonds efficiently (see scheme; DMAc= N.N-dimethylacetamide, bpy = 2,2′-bipyridine). This catalysis represents a new avenue for using organosilanes in the catalytic C-H functionalization chemistry.
Hachiya, Hitoshi,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
supporting information; body text
p. 2202 - 2205
(2010/06/18)

Cobalt-catalyzed addition of azoles to alkynes
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
supporting information; experimental part
p. 4180 - 4183
(2010/11/19)

CCR5 ANTAGONISTS AS THERAPEUTIC AGENTS
The present invention relates to compounds useful in the treatment of CCR5-related diseases and disorders, for example, useful in the inhibition of HIV replication, the prevention or treatment of an HIV infection, and in the treatment of the resulting acq
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Page/Page column 26-27

(2009/07/17)

Synthesis of 2,5-diaryloxazoles through van Leusen reaction and copper-mediated direct arylation
The direct arylation of 5-aryloxazoles, prepared by the van Leusen reaction, with various aryl iodides is effectively promoted by a system of CuI combined with PPh3 and Na2CO3 as a ligand and a base, respectively, in DMF to produce the corresponding 2,5-diaryloxazoles in good yields.
Yoshizumi, Tomoki,Satoh, Tetsuya,Hirano, Koji,Matsuo, Daisuke,Orita, Akihiro,Otera, Junzo,Miura, Masahiro
supporting information; body text
p. 3273 - 3276
(2009/08/09)

Synthesis of 2-TIPS-oxazol-5-ylboronic acid pinacol ester: efficient route to 5-(het)aryloxazoles via Suzuki cross-coupling reaction
A facile synthetic route to the new 2-TIPS-oxazol-5-ylboronic acid pinacol ester was described herein. Its reactivity toward Suzuki cross-coupling reaction was studied to provide various 5-(het)aryloxazoles. A wide range of functions on the aryl moiety ar
Primas, Nicolas,Bouillon, Alexandre,Lancelot, Jean-Charles,Rault, Sylvain
scheme or table
p. 6348 - 6353
(2009/12/04)

TRPV1 ANTAGONISTS
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 17

(2009/05/28)

Ligandless microwave-assisted Pd/Cu-catalyzed direct arylation of oxazoles
(Chemical Equation Presented) An efficient microwave-assisted palladium/copper co-mediated direct arylation of oxazoles with aryl bromides under ligandless conditions has been developed. The method is functional group tolerant and provides rapid access to medicinally relevant compounds in good yields. Coupled to the van Leusen oxazole ring synthesis, this methodology is illustrated by an expedient two-step synthesis of the four 2,5-diaryloxazole alkaloids texamine, texaline, balsoxin, and O-Me-halfordinol from commercially available starting materials.
Besselievre, Francois,Mahuteau-Betzer, Florence,Grierson, David S.,Piguel, Sandrine
p. 3278 - 3280
(2008/09/19)

Stereoselective direct copper-catalyzed alkenylation of oxazoles with bromoalkenes
(Chemical Equation Presented) A copper-catalyzed direct alkenylation of oxazoles with bromoalkenes has been developed. The method is both regio- and stereoselective and tolerates a variety of functional groups. A wide range of 2-E-vinyl-substituted oxazoles were obtained in high yields including the highly fluorescent alkaloid annuloline.
Besselievre, Francois,Piguel, Sandrine,Mahuteau-Betzer, Florence,Grierson, David S.
scheme or table
p. 4029 - 4032
(2009/06/18)

Oxazole synthesis with minimal purification: Synthesis and application of a ROMPgel tosmic reagent
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.
p. 271 - 273
(2007/10/03)

Solution-phase parallel oxazole synthesis with TosMIC
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
p. 5637 - 5638
(2007/10/03)

Synthesis and reactivities of 1-(isocyanomethyloxy)benzotriazole as a new source of isocyanomethyl synthon
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
p. 1369 - 1371
(2007/10/03)

Benzotriazol-1-ylmethyl isocyanide, a new synthon for CH-N=C transfer. Syntheses of α-hydroxyaldehydes, 4-ethoxy-2-oxazolines and oxazoles
Readily prepared benzotriazol-1-ylmethyl isocyanide (BetMIC) reacts under mild conditions with ketones and aldehydes, to afford oxazolines (convertible into α-hydroxyaldehydes) and oxazoles, respectively.
Katritzky,Chen,Yannakopoulou,Lue
p. 6657 - 6660
(2007/10/02)