- General α-Amino 1,3,4-Oxadiazole Synthesis via Late-Stage Reductive Functionalization of Tertiary Amides and Lactams**
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An iridium-catalyzed reductive three-component coupling reaction for the synthesis of medicinally relevant α-amino 1,3,4-oxadiazoles from abundant tertiary amides or lactams, carboxylic acids, and (N-isocyanimino) triphenylphosphorane, is described. Proceeding under mild conditions using (3)2) and tetramethyldisiloxane to access the key reactive iminium ion intermediates, a broad range of α-amino 1,3,4-oxadiazole architectures were accessed from carboxylic acid feedstock coupling partners. Extension to α-amino heterodiazole synthesis was readily achieved by exchanging the carboxylic acid coupling partner for C-, S-, or N-centered Br?nsted acids, and provided rapid and modular access to these desirable, yet difficult-to-access, heterocycles. The high chemoselectivity of the catalytic reductive activation step allowed late-stage functionalization of 10 drug molecules, including the synthesis of heterodiazole-fused drug–drug conjugates.
- Dixon, Darren J.,Matheau-Raven, Daniel
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- COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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The present specification provides a compound represented by chemical formula 1 and an organic light emitting device including the same. The compound may improve lifespan characteristics of the organic light emitting device.
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Paragraph 0258-0261; 0266-0269
(2021/01/29)
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- Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds
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The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.
- Chang, Xiao-Yong,Chen, Ji-Jun,Gu, Qiang-Shuai,Jiang, Sheng-Peng,Li, Zhong-Liang,Liu, Lin,Liu, Xiao-Dong,Liu, Xin-Yuan,Su, Xiao-Long,Wang, Fu-Li,Yang, Chang-Jiang,Ye, Liu
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supporting information
p. 380 - 384
(2020/10/30)
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- [4u202f+u202f1] Cyclization of benzohydrazide and ClCF2COONa towards 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5
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A facile synthesis of 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5 via [4 + 1] cyclization of ClCF2COONa with non-amine compounds containing amino groups is developed. Of note, this is the first time that halofluorinated compounds are used as C1 synthon to construct deuterated nitrogen-heterocyclic compounds. The current protocol features simple operation, readily accessible raw materials, wide substrate scope and valuable products
- Li, Xin,Mu, Shiqiang,Song, Qiuling,Wang, Ya
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supporting information
(2021/09/20)
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- Ligand-Enabled Palladium-Catalyzed Through-Space C?H Bond Activation via a Carbopalladation/1,4-Pd Migration/C?H Functionalization Sequence
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We report, herein, a palladium-catalyzed cascade comprising carbopalladation, 1,4-Pd-migration and C(sp2)?C(sp2) bond formation to construct a variety of bis-heterocyclic frameworks in a single operational step. The methodology provi
- Chen, Su,Ranjan, Prabhat,Ramkumar, Nagarajan,Van Meervelt, Luc,Van der Eycken, Erik V.,Sharma, Upendra K.
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supporting information
p. 14075 - 14079
(2020/10/12)
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- Functionalization of 1,3,4-Oxadiazoles and 1,2,4-Triazoles via Selective Zincation or Magnesiation Using 2,2,6,6-Tetramethylpiperidyl Bases
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We report the metalation of the 1,3,4-oxadiazole and 1,2,4-triazole scaffolds via regioselective zincation or magnesiation using the TMP bases (TMP = 2,2,6,6-tetramethylpiperidyl) TMP2Zn·2LiCl, TMP2Zn·2MgCl2·2LiCl, TMPMgCl
- Schw?rzer, Kuno,Tüllmann, Carl Phillip,Gra?l, Simon,Górski, Bartosz,Brocklehurst, Cara E.,Knochel, Paul
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supporting information
p. 1899 - 1902
(2020/03/03)
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- TiCl4 mediated facile synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles
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An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles has been developed. Various hydrazides or thionyl hydrazides readily react with DMA derivatives in the presence of TiCl4 as a catalyst to afford the desired products. This protocol provides a simple and economical procedure that affords the target products with good yields and wide substrate scope.
- Zhang, Lin,Yu, Yu,Tang, Qiang,Yuan, Jianyong,Ran, Dongzhi,Tian, Binghua,Pan, Tao,Gan, Zongjie
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p. 423 - 431
(2019/12/27)
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- MONITORING AND DOSAGE CONTROL OF TAGGED TREATMENT POLYMERS IN INDUSTRIAL WATER SYSTEMS
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The present invention relates to a fluorescently-tagged (co)polymer useful as a scale inhibitor in industrial water systems. Said (co)polymer comprises a (i) reactive fluorescent compound selected from a diazole compound (ii) at least one monoethylenicall
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Page/Page column 13; 14
(2019/02/17)
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- TAGGED TREATMENT POLYMERS FOR MONITORING ANTISCALANT CONCENTRATIONS IN INDUSTRIAL WATER SYSTEMS
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The present invention relates to a fluorescently-tagged (co)polymer useful as a scale inhibitor in industrial water systems. Said (co)polymer comprises a (i) reactive fluorescent compound selected from a diazole compound (ii) at least one monoethylenicall
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Page/Page column 13; 14
(2019/02/15)
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- Two platinum(ii) complexes with a 4-phenyl-4: H -1,2,4-triazole derivative as an ancillary ligand for efficient green OLEDs
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Two new cyclometalated platinum(ii) complexes ((TN3T)Pt(dptp), (4tfmppy)Pt(dptp)) with 2′,6′-bis(trifluoromethyl)-2,3′-bipyridine (TN3T) and 4-trifluoromethylphenylpyridine (4tfmppy) as the cyclometalated ligands and the nitrogen het
- Lu, Guang-Zhao,Tu, Zhen-Long,Liu, Liang,Zheng, You-Xuan,Zhao, Yue
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p. 1892 - 1899
(2019/03/23)
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- Two green iridium(iii) complexes containing the electron-transporting group of 4-phenyl-4H-1,2,4-triazole for highly efficient OLEDs
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Two new iridium(iii) cyclometalated complexes (Ir-TN3T and Ir-TN4T) with 2′,6′-bis(trifluoromethyl)-2,3′-bipyridine (TN3T) and 2′,6′-bis(trifluoromethyl)-2,4′-bipyridine (TN4T) as the cyclometalated ligands and
- Lu, Guang-Zhao,Liu, Liang,Tu, Zhen-Long,Zhou, Yong-Hui,Zheng, You-Xuan
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p. 2022 - 2028
(2019/02/24)
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- DMF as Methine Source: Copper-Catalyzed Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles
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An unprecedented Cu-catalyzed direct annulation of hydrazides with N,N-dimethylformamide (DMF) was developed, providing an efficient synthesis of valuable 1,3,4-oxadiazoles. This process features the short reaction time and can be safely conducted on gram scale. The reaction also facilitated the convenient synthesis of 1,3,4-oxadiazole-2(3H)-ones. Moreover, the mechanistic studies suggest that the source of CH is from the N-methyl group of DMF. (Figure presented.).
- Wang, Shoucai,Wang, Kai,Kong, Xiangfei,Zhang, Shuhua,Jiang, Guangbin,Ji, Fanghua
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p. 3986 - 3990
(2019/07/31)
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- Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles
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A novel methodology for general and chemoselective preparation of non-symmetric 1,3,4-oxadiazoles is developed. This unusual reaction proceeds via polyphosphoric acid-assisted activation of nitroalkanes towards nucleophilic attack with acylhydrazides.
- Aksenov, Alexander V.,Khamraev, Vladislav,Aksenov, Nicolai A.,Kirilov, Nikita K.,Domenyuk, Dmitriy A.,Zelensky, Vladimir A.,Rubin, Michael
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p. 6636 - 6642
(2019/03/14)
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- Method for one-step construction of 2-phenyl-1,3,4-oxadiazole by DMF (N,N-dimethylformamide) as carbon source
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The invention discloses a method for one-step construction of 2-phenyl-1,3,4-oxadiazole by DMF (N,N-dimethylformamide) as a carbon source. According to the method, benzoyl hydrazine is taken as a reaction raw material, the DMF is taken as the carbon sourc
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Paragraph 0004; 0012; 0016-0023
(2019/02/04)
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- Palladium-Catalyzed Domino Allenamide Carbopalladation/Direct C-H Allylation of Heteroarenes: Synthesis of Primprinine and Papaverine Analogues
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Palladium-catalyzed intramolecular carbopalladation onto allenamides completed by direct C-H allylation of heterocycles is studied. The domino construction/heteroarylation of isoquinolone process is first achieved. A general three-step one-pot strategy, i
- Hédouin, Jonathan,Schneider, Cédric,Gillaizeau, Isabelle,Hoarau, Christophe
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supporting information
p. 6027 - 6032
(2018/10/05)
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- Spectral-Luminescent Properties of 2-Aryl-1,3,4-oxadiazoles
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Refluxing equimolar amounts of acylhydrazides with triethyl orthoformate in o-xylene yielded 2-aryl-1,3,4-oxadiazoles luminescing with high quantum yields in polar and nonpolar solvents (λm fl ax 299–349 nm, φ 0.20–0.62). The only exception was 2-(1,3,4-o
- Mikhailov,Artyushkina, Yu. M.,Dushenko,Mikhailova,Revinskii, Yu. V.,Minkin
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p. 602 - 604
(2018/04/23)
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- Synthesis of 1,3,4-Oxadiazoles via Annulation of Hydrazides and Benzene-1,3,5-triyl Triformate under Metal-Free Conditions
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A new and efficient method for the synthesis of 1,3,4-oxadiazoles via the annulation of hydrazides with benzene-1,3,5-triyl triformate (TFBen) under metal-free conditions is reported. A broad range of hydrazides were transformed into the corresponding 1,3
- Yin, Zhiping,Power, Dennis J.,Wang, Zechao,Stewart, Scott G.,Wu, Xiao-Feng
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supporting information
p. 3238 - 3242
(2018/04/24)
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- Ligand-free Cu(ii)-mediated aerobic oxidations of aldehyde hydrazones leading to N,N′-diacylhydrazines and 1,3,4-oxadiazoles
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A Cu(ii)-mediated synthesis of N,N′-diacylhydrazines and 1,3,4-oxadiazoles from aldehyde hydrazones has been developed. This is the first time that the synthesis of N,N′-diacylhydrazines and 1,3,4-oxadiazoles using N,N-dimethylamides as the acylation reagent and O2 in air as the oxidation reagent is reported. These reactions offered several advantages including simple workups, ligand-free inexpensive metal salts as mediators, high yields, and wide scope of substrates.
- Liu, Lei,Feng, Suliu
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supporting information
p. 2585 - 2592
(2017/04/03)
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- (NHC)Cu-Catalyzed Mild C-H Amidation of (Hetero)arenes with Deprotectable Carbamates: Scope and Mechanistic Studies
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Primary arylamines are an important unit broadly found in synthetic, biological, and materials science. Herein we describe the development of a (NHC)Cu system that mediates a direct C-H amidation of (hetero)arenes by using N-chlorocarbamates or their sodio derivatives as the practical amino sources. A facile stoichiometric reaction of reactive copper-aryl intermediates with the amidating reagent led us to isolate key copper arylcarbamate species with the formation of a C-N bond. The use of tBuONa base made this transformation catalytic under mild conditions. The present (NHC)Cu-catalyzed C-H amidation works efficiently and selectively on a large scale over a range of arenes including polyfluorobenzenes, azoles, and quinoline N-oxides. Deprotection of the newly installed carbamate groups such as Boc and Cbz was readily performed to afford the corresponding primary arylamines.
- Xie, Weilong,Yoon, Jung Hee,Chang, Sukbok
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supporting information
p. 12605 - 12614
(2016/10/07)
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- BLUE LUMINESCENT COMPOUNDS
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There is provided a compound having Formula II In Formula II: R1 and R3 are the same of different and can be alkyl, branched alkyl, cyclic alkyl, silyl, aryl, deuterated alkyl, deuterated branched alkyl, deuterated cyclic alkyl, deut
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- Iodine-Mediated Domino Oxidative Cyclization: One-Pot Synthesis of 1,3,4-Oxadiazoles via Oxidative Cleavage of C(sp2)-H or C(sp)-H Bond
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An I2-promoted, metal-free domino protocol for one-pot synthesis of 1,3,4-oxadiazoles has been developed via oxidative cleavage of C(sp2)-H or C(sp)-H bonds, followed by cyclization and deacylation. In this reaction, the use of K2CO3 as a base is found to be an essential factor in the cyclization and the C-C bond cleavage. This procedure proceeded smoothly in moderate to high yields with good functional group compatibility.
- Fan, Yuxing,He, Yongqin,Liu, Xingxing,Hu, Ting,Ma, Haojie,Yang, Xiaodong,Luo, Xinliang,Huang, Guosheng
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p. 6820 - 6825
(2016/08/16)
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- Transition-metal-free oxidative iodination of 1,3,4-oxadiazoles
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Transition-metal-free oxidative iodination of 2-substituted 1,3,4-oxadiazoles was achieved by using sodium iodide as the halide source and Selectfluor as the oxidant. Variously substituted products were obtained in moderate to good yields under operationa
- Dannenberg, Carl Albrecht,Bizet, Vincent,Zou, Liang-Hua,Bolm, Carsten
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supporting information
p. 77 - 80
(2015/02/02)
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- Direct C-H iodination of 1,3-azoles catalysed by CuBr2
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A mild method was developed for the direct C-H iodination of 1,3-azoles catalysed by CuBr2. Compared with the traditional metalation/iodination sequences carried out with nBuLi or TMPLi (TMP = 2,2,6,6-tetramethylpiperidino), a relatively weaker base, LiOtBu, was used in the presence of 1,10-phenanthroline. Five series of 1,3-azoles, including benzoxazole, benzothiozole, N-methyl-benzoimidazole, 5-phenyloxazole and 2-phenyl-1,3,4-oxadiazole were tested and afforded the corresponding iodination products.
- Zhao, Xia,Ding, Fang,Li, Jingyu,Lu, Kui,Lu, Xiaoyu,Wang, Bin,Yu, Peng
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supporting information
p. 511 - 513
(2015/02/19)
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- Highly Quantum Efficient Phosphorescent Sky Blue Emitters Based on Diastereomeric Iridium(III) Complexes of Atropisomeric 5-Aryl-4H-1,2,4-triazole Ligands
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(Chemical Equation Presented) Homoleptic fac-IrIIIL3 complexes of 5-aryl-4H-1,2,4-triazole ligands are sky blue emitters. When unsymmetrically substituted, the triazole ligands exhibit atropisomerism, and upon cyclometalation to Ir(I
- Feldman, Jerald,Vo, Giang D.,McLaren, Charles D.,Gehret, Troy C.,Park, Kyung-Ho,Meth, Jeffrey S.,Marshall, Will J.,Buriak, Joseph,Bryman, Lois M.,Dobbs, Kerwin D.,Scholz, Thomas H.,Zane, Steve G.
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supporting information
p. 3665 - 3669
(2015/08/19)
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- Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles via Oxidative C(CO)-C(Methyl) Bond Cleavage of Methyl Ketones
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A new strategy for the synthesis of 1,3,4-oxadiazoles was established through direct annulation of hydrazides with methyl ketones. It was found that the use of K2CO3 as a base achieves an unexpected and highly efficient C-C bond clea
- Gao, Qinghe,Liu, Shan,Wu, Xia,Zhang, Jingjing,Wu, Anxin
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p. 2960 - 2963
(2015/06/30)
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- Efficient synthesis of 1,3,4-oxadiazoles promoted by NH4Cl
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An efficient and inexpensive approach to the synthesis of 2-substituted and 2,5-disubstituted 1,3,4-oxadiazoles from arylhydrazides and orthoesters is reported using catalytic NH4Cl. The conditions are mild, and thus, compatible with a variety of functional groups. The optimized reaction is performed using 30 mol % of NH4Cl in 100% EtOH and is generally complete within 1 h for non-aromatic orthoesters and 2-10 h for aromatic orthoesters. The reaction permits both electron-releasing and electron-withdrawing groups on the arylhydrazide substrate. Most products are formed in high yields and require only minimal purification. Compared with earlier reports, the current reactions proceed in shorter time and require less of the orthoester.
- Gnanasekaran, Krishna Kumar,Nammalwar, Baskar,Murie, Maeghan,Bunce, Richard A.
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supporting information
p. 6776 - 6778
(2015/01/09)
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- BLUE LUMINESCENT COMPOUNDS
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There is provided a compound having Formula II. In Formula II: R1 can be alkyl having 1-6 carbons, silyl having 3-6 carbons, or a deuterated analog thereof; R2 can be alkyl, silyl, aryl, or a deuterated analog thereof; a and c are the same or different and are an integer from 0-4; and b is an integer from 0-5.
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Page/Page column 32
(2014/06/23)
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- Novel, fast and efficient one-pot sonochemical synthesis of 2-aryl-1,3,4-oxadiazoles
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Ultrasound promoted synthesis of 2-aryl-1,3,4-oxadiazoles at ambient temperature is reported. The remarkable features of the new procedure are shorter reaction time, excellent yields, cleaner reaction profile and simple experimental and workup procedure.
- Rouhani, Morteza,Ramazani, Ali,Joo, Sang Woo
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p. 262 - 267
(2013/10/01)
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- Pd(OAc)2 catalyzed C-H activation of 1,3,4-oxadiazoles and their direct oxidative coupling with benzothiazoles and aryl boronic acids using Cu(OAc)2 as an oxidant
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The first direct oxidative coupling of 1,3,4-oxadiazoles with benzothiazoles has been accomplished using Pd(OAc)2 as a catalyst and Cu(OAc)2 as an oxidant. The similar combination of the catalyst and the oxidant has also been applied for direct arylation of 1,3,4-oxadiazoles with aryl boronic acids. Several novel oxadiazole derivatives have been prepared in high yields following both the methods.
- Salvanna,Reddy, Gandolla Chinna,Das, Biswanath
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supporting information
p. 2220 - 2225
(2013/03/13)
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- Synthesis and evaluation of in vivo anticonvulsant activity of 2,5-disubstituted-1,3,4-oxadiazole derivatives
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A series of new 2,5-disubstituted-1,3,4-oxadiazole derivatives 8(a-o) was synthesized by the reaction of 1-(5-phenyl-1,3,4-oxadiazol-2-yl)piperazine with various sulfonyl chlorides. The synthesized compounds were characterized by elemental analyses,
- Harish, Kikkeri P.,Mohana, Kikkeri N.,Mallesha, Lingappa,Veeresh,Madhava Reddy,Kumar, Nagula Naresh
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p. 783 - 791
(2013/12/04)
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- Copper-catalyzed direct cross coupling of 1,3,4-oxadiazoles with trans-β-halostyrenes: Synthesis of 2-E-vinyl 1,3,4-oxadiazoles
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The first direct C-H alkenylation of 1,3,4-oxadiazoles with trans-β-halo olefinic system has been carried out using a combination of CuI/DMEDA as a catalyst. A wide range of 2-E-vinyl-substituted oxadiazoles were obtained in high yields (85-93%).
- Das, Biswanath,Reddy, Gandolla Chinna,Balasubramanyam, Penagaluri,Salvanna
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supporting information; experimental part
p. 300 - 305
(2012/01/05)
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- Copper-mediated C-H activation of 1,3,4-oxadiazoles with 1,1-dibromo-1-alkenes using PEG-400 as a solvent medium: Distinct approach for the alkynylation of 1,3,4-oxadiazoles
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The direct C-H alkynylation of 1,3,4-oxadiazoles with 1,1-dibromo-1-alkenes has been accomplished by using a combination of CuBr/LiOtBu in PEG-400 (a green solvent) at 80 °C. The products were formed in high yields (73-86%) in 2 h. No additional ligand or volatile solvent was required and the conversion was ecofriendly. The direct C-H alkynylation of 1,3,4-oxadiazoles with 1,1-dibromo-1-alkenes has been accomplished by using a combination of CuBr/LiOtBu in PEG-400 (a green solvent) at 80 °C. The products were formed in high yields (73-86%) in 2 h. No additional ligand or volatile solvent was required and the conversion was ecofriendly. Copyright
- Reddy, Gandolla Chinna,Balasubramanyam, Penagaluri,Salvanna,Das, Biswanath
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supporting information; experimental part
p. 471 - 474
(2012/03/08)
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- Transition metal-free direct C-H bond thiolation of 1,3,4-oxadiazoles and related heteroarenes
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A convenient transition metal-free procedure for the direct thiolation of 1,3,4-oxadiazole C-H bonds using diaryl disulfides has been developed. Other substrates including indole, benzothiazole, N-phenylbenzimidazole, and caffeine were also thiolated in this manner, providing the corresponding products in good to excellent yields. This journal is
- Zou, Liang-Hua,Reball, Jens,Mottweiler, Jakob,Bolm, Carsten
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supporting information
p. 11307 - 11309,3
(2020/10/15)
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- Novel series of 3-amino-N-(4-aryl-1,1-dioxothian-4-yl)butanamides as potent and selective dipeptidyl peptidase IV inhibitors
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A series of novel 3-amino-N-(4-aryl-1,1-dioxothian-4-yl)butanamides were investigated as dipeptidyl peptidase IV (DPP-4) inhibitors. Introduction of a 4-phenylthiazol-2-yl group showed highly potent DPP-4 inhibitory activity. Among various derivatives, (3R)-3-amino-N-(4-(4-phenylthiazol-2-yl)-tetrahydro-2H- thiopyran-4-yl)-4-(2,4,5-trifluorophenyl)butanamide 1,1-dioxide (30) reduced blood glucose excursion in an oral glucose tolerance test by oral administration.
- Nitta, Aiko,Fujii, Hideaki,Sakami, Satoshi,Satoh, Mikiya,Nakaki, Junko,Satoh, Shiho,Kumagai, Hiroki,Kawai, Hideki
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p. 7036 - 7040
(2013/01/15)
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- A metal-free route to 2-aminooxazoles by taking advantage of the unique ring opening of benzoxazoles and oxadiazoles with secondary amines
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Toss an amine into the ring: A new metal-free protocol for the amination of oxazoles has been developed by using iodobenzene diacetate to couple various oxazoles with amines (see scheme). The reaction proceeds through a ring-opening and subsequent ring-closing pathway. The optimal conditions are very mild and the substrate scope is broad, producing a range of 2-aminooxazoles, an important pharmacophore with high bioactivity. Copyright
- Joseph, Jomy,Kim, Ji Young,Chang, Sukbok
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supporting information; experimental part
p. 8294 - 8298
(2011/08/21)
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- Amination of benzoxazoles and 1,3,4-oxadiazoles using 2,2,6,6- tetramethylpiperidine-N-oxoammonium tetrafluoroborate as an organic oxidant
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No transition metals are necessary to convert benzoxazoles and 1,3,4-oxadiazoles into the corresponding pharmacologically interesting 2-aminated heterocycles by formal direct C(2)-amination using tetramethylpiperidine-N-oxoammonium tetrafluoroborate (TEMPO+BF 4-) as an oxidant (see scheme; TEMP=2,2,6,6- tetramethylpiperidine; TfOH=trifluoromethanesulfonic acid).
- Wertz, Sebastian,Kodama, Shintaro,Studer, Armido
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supporting information; experimental part
p. 11511 - 11515
(2012/01/11)
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- 17O NMR studies of substituted 1,3,4-oxadiazoles
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Three series of substituted 1,3,4-oxadiazoles were studied by 17O NMR spectroscopy. Chemical shifts values were correlated with empirical Hammett parameters as well as calculated bond lengths and chemical shielding values.
- Gierczyk, Blazej,Zalas, MacIej,Kazmierczak, Marcin,Grajewski, Jakub,Pankiewicz, Radoslaw,Wyrzykiewicz, Bozena
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scheme or table
p. 648 - 654
(2012/01/06)
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- POLYCYCLIC COMPOUNDS AS LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
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Described herein are compounds that are antagonists of lysophosphatidic receptor(s). Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists, alone and in combination with other compounds, for treating LPA-dependent or LPA-mediated conditions or diseases.
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Page/Page column 28
(2011/04/24)
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- Cobalt- and manganese-catalyzed direct amination of azoles under mild reaction conditions and the mechanistic details
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A bonding moment: A new cobalt- or manganese-catalyzed amination of azoles has been developed using peroxide and an acid additive to couple various types of azoles with ammonia, and primary or secondary amines (see scheme). The catalyst loadings are low, the optimal reaction conditions are mild, and the substrate scope is broad. The product azoles are an important pharmacophore of high biological activity. Copyright
- Kim, Ji Young,Cho, Seung Hwan,Joseph, Jomy,Chang, Sukbok
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supporting information; experimental part
p. 9899 - 9903
(2011/02/25)
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- A new entry of amination reagents for heteroaromatic C-H bonds: Copper-catalyzed direct amination of azoles with chloroamines at room temperature
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Chloroamine serves as an efficient amination reagent to the heteroaromatic C-H bond of azole under copper catalysis even at room temperature. This catalysis enables a rapid and concise construction of aminoazoles of great interest in biological and medicinal chemistry.
- Kawano, Tsuyoshi,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information; experimental part
p. 6900 - 6901
(2010/07/05)
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- Greener and rapid access to bio-active heterocycles: one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles
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A novel one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles by condensation of acid hydrazide and triethyl orthoalkanates under microwave irradiations is reported. This green protocol was catalyzed efficiently by solid supported NafionNR50 and phosphorus pentasulfide in alumina (P4S10/Al2O3) with excellent yields.
- Polshettiwar, Vivek,Varma, Rajender S.
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p. 879 - 883
(2008/09/17)
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- Alum (KAl(SO4)2 ? 12H2O): An efficient and inexpensive catalyst for the one-pot synthesis of 1,3,4-oxadiazoles under solvent-free conditions
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Alum (KAl(SO4)2 ? 12H2O) catalyzed the efficient synthesis of mono- and disubstituted 1,3,4-oxadiazoles by the condensation of acyl hydrazides with orthoesters under solvent-free conditions at 100°C. This methodology offers significant improvements for the synthesis of oxadiazoles with regard to the yield of products, simplicity in operation, inexpensive reagents, and green aspects by avoiding toxic catalysts and solvents.
- Dabiri, Minoo,Salehi, Peyman,Baghbanzadeh, Mostafa,Bahramnejad, Mahboobeh
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p. 1253 - 1255
(2008/03/28)
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- Silica sulfuric acid: An efficient and versatile acidic catalyst for the rapid and ecofriendly synthesis of 1,3,4-oxadiazoles at ambient temperature
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A rapid and green synthesis of 2,5-disubstituted 1,3,4-oxadiazoles is reported. The title compounds were prepared by the reaction of different acyl hydrazides and orthoesters in the presence of silica sulfuric acid under solvent-free conditions. In this new process, reactions were run at ambient temperature and completed in a short period of time with high yields. Copyright Taylor & Francis Group, LLC.
- Dabiri, Minoo,Salehi, Peyman,Baghbanzadeh, Mostafa,Zolfigol, Mohammad Ali,Bahramnejad, Mahboobeh
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p. 1201 - 1209
(2008/02/01)
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- Novel molecular structures with controllable electron conducting properties
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Aromatic and heteroaromatic molecular structures with controllable electron conducting properties are derived from the incorporation of electron active substituents in selective positions. Such compounds can form self-assembled layers on metal or other su
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- The reaction of (N-isocyanimino)triphenylphosphorane with benzoic acid derivatives: a novel synthesis of 2-aryl-1,3,4-oxadiazole derivatives
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The reactions of benzoic acid derivatives with (N-isocyanimino)triphenylphosphorane proceed smoothly at room temperature to afford 2-aryl-1,3,4-oxadiazoles in high yields.
- Souldozi, Ali,Ramazani, Ali
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p. 1549 - 1551
(2008/02/03)
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- Keto-1,3,4-oxadiazoles as cathepsin K inhibitors
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We have prepared a series of cathepsin K inhibitors bearing the keto-1,3,4-oxadiazole warhead capable of forming a hemithioketal complex with the target enzyme. By modifying binding moieties at the P1, P2, and prime side positions of the inhibitors, we have achieved selectivity over cathepsins B, L, and S, and have achieved sub-nanomolar potency against cathepsin K. This series thus represents a promising chemotype that could be used in diseases implicated by imbalances in cathepsin K activity such as osteoporosis.
- Palmer, James T.,Hirschbein, Bernard L.,Cheung, Harry,McCarter, John,Janc, James W.,Yu, Z. Walter,Wesolowski, Gregg
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p. 2909 - 2914
(2008/09/21)
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- HALOALKYL CONTAINING COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS
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The application is directed to haloalkyl-substituted compounds of Formula (I), wherein R1, R1a, R2, R3, R4’ and E are as defined in the claims. The compounds are inhibitors of cysteine proteases, in p
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Page/Page column 54
(2010/02/11)
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- AMIDINO COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS
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The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.
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Page/Page column 23-24
(2010/02/12)
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- SILINANE COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS
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The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is also directed to pharmaceutical compositions comprising these compounds and processes for preparing them. The present invention is also directed to the use of these inhibitors in combination with a therapy that causes a deleterious immune response in patients receiving the therapy.
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Page/Page column 59
(2008/06/13)
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- PROTEASOME INHIBITORS
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The present invention is directed to compounds that are proteasome inhibitors, pharmaceutical composition comprising such compounds and methods of treating diseases mediated by unregulated proteasome activity.
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