64414-11-5Relevant academic research and scientific papers
Facile synthesis of 2-benzoxazoles via CuI/2,2'-bipyridine catalyzed intramolecular C–O coupling of 2-haloanilides
Venu Saranya, Thachora,Rajan Sruthi, Pambingal,Anas, Saithalavi
, p. 297 - 307 (2019/01/18)
Development of newer methods for the synthesis of Benzoxazoles has of greater interest due to their wide range of biological activities and pharmaceutical importance. We herein report a facile and general method for the synthesis of 2-substituted Benzoxazoles via copper catalyzed intramolecular C–O cross-coupling of 2-haloanilides. A combination of CuI (5 mol%), 2,2'-bipyridine (10 mol%), Cs2CO3 (2 equiv.) in DMF solvent with 4 ? molecular sieves at 140 °C, illustrated the scope for tuning the reactivity of 2-haloanilides toward the selective formation of a series of 2-alkyl benzoxazole derivatives in moderate to good yields. This is the first systematic study using CuI/2,2'-Bipyridine as the catalytic system for the synthesis of 2-substituted Benzoxazoles. The outcome of the reaction was found to be significantly influenced by the aromatic and amide substituents of 2-haloanilides.
NOVEL ULK1 INHIBITORS AND METHODS USING SAME
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Page/Page column 236, (2016/03/22)
In certain aspects, the invention provides a method for treating a disease or condition in a subject, the method comprising co-administering to a subject in need thereof a therapeutically effective amount of at least one ULK1-inhibiting pyrimidine, and a therapeutically effective amount of an mTOR inhibitor.
Synthesis of 2-oxazolines and related N-containing heterocycles using [Et2NSF2]BF4 as a cyclodehydration agent
Pouliot, Marie-France,Angers, Laetitia,Hamel, Jean-Denys,Paquin, Jean-Fran?ois
supporting information; experimental part, p. 4121 - 4123 (2012/08/28)
The preparation of 2-oxazolines and related N-containing heterocycles from the corresponding hydroxyamides using XtalFluor-E ([Et2NSF 2s]BF4) as a cyclodehydration agent is described. A wide range of heterocycles are obtai
Ortho-directed functionalization of arenes using magnesate bases
Bellamy, Estelle,Bayh, Omar,Hoarau, Christophe,Trecourt, Francois,Queguiner, Guy,Marsais, Francis
supporting information; experimental part, p. 7043 - 7045 (2010/11/02)
Ortho-directed functionalisation of arenes using lithium alkylmagnesate bases were achieved, demonstrating the potential use of arylmagnesates as suitable arylanions, without a further transmetallation step, for challenging functionalizations such as fluorination, hydroxylation, arylation, vinylation and alkylation through epoxide ring-opening.
Regioselective synthesis of 3-hydroxyorthanilic acid and its biotransformation into a novel phenoxazinone dye by use of laccase
Bruyneel, Frederic,Enaud, Estelle,Billottet, Ludovic,Vanhulle, Sophie,Marchand-Brynaert, Jacqueline
, p. 72 - 79 (2008/09/17)
A natural phenoxazinone derivative, cinnabarinic acid (2, CA, R = CO 2H), could be obtained in vitro with the aid of purified laccase from the fungi Pycnoporus cinnabarinus by oxidative dimerization of 3-hydroxyanthranilic acid (1, 3-HAA, R = C
Phosphorus in organic synthesis. Acyloxyphosphonium salts as chemoselective acylating reagents
Froyen, Paul
, p. 5359 - 5362 (2007/10/03)
Acyloxytriphenylphosphonium salts 1 prepared in situ react with a variety of aminophenols to give the corresponding amides in excellent yields. At -25°N-acylated products are formed exclusively, whereas 0°some O-acylated products are observed. 1 is also a
Highly chemoselective acylation of substituted aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione
Dai, Wei-Min,Cheung, Yuk King,Tang, Kit Wan,Choi, Pui Yiu,Chung, Suet Lam
, p. 12263 - 12276 (2007/10/02)
A general procedure for chemoselective acylation of substituted aminophenols has been developed. The N-acetylated products 7 and 10a-h were prepared by treating the aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione (1) in refluxing THF in 70-100% yield. The esters 8 and 13d,b,j of 3- and 4-amino phenols could be obtained in 70-94% yield by treating with NaH and 1.
Tertiary Amine-Catalyzed Acyl Group Exchange Reaction of N,O-Diacyl-o-aminophenols. Its Mechanism and Factors Determining the Relative Stability of Acyl Exchanged Isomer Pairs
Sakurai, Tadamitsu,Kojima, Shuichi,Inoue, Hiroyasu
, p. 3141 - 3148 (2007/10/02)
Acyl substituent effects on the equilibrium and rate constants for the acyl group exchange reactions of various N,O-diacyl-o-aminophenols have been investigated in solvents with different polarities.It was found that the relative stability of acyl exchanged isomer pairs is determined solely by the inductive effect of acyl groups, provided that the steric hindrance of acyl substituents bonded to amide nitrogen affects the stability to the same extent.The importance of steric hindrance exerted by a bulky acyl group in determining the relative stability was demonstrated by analyzing the correlation between the standard free energy change (ΔG0) and pKa, which were used as the measure of the relative stability of isomer pairs and of the electron-with drawing ability of acyl groups, respectively.On the other hand, the logarithms of catalytic rate constants for the acyl migration reactions were correlated well to the pKa values.In addition to this finding, a large negative value of activation entropy (ΔS=-160 J K-1 mol-1) and the Broensted coefficient β of 0.65 for the reaction of N,O-(acetyl)-(1-naphthoyl) pair of N,O-diacyl-o-aminophenol provide a definitive evidence for the rate-determining proton transfer from this derivative to amine catalyst in the transition state.
2-t-BUTYL-5-CHLORO-6-NITROBENZOXAZOLE: A PRACTICAL SYNTHETIC INTERMEDIATE FOR 4-ARYLOXY-5-NITRO-2-AMINOPHENOLS
Ono, Mitsunori,Yamakawa, Katsuyoshi,Kobayashi, Hidetoshi,Itoh, Isamu
, p. 881 - 884 (2007/10/02)
On the examination of the anomalous reactivities of several nitrobenzoxazole derivatives 2a-e toward acids and bases it has been found that 2-t-butyl-5-chloro-6-nitrobenzoxazole 2c serves as one of the most convenient and practical synthetic intermediates for 4-aryloxy-5-nitro-2-aminophenols.
