- [4u202f+u202f1] Cyclization of benzohydrazide and ClCF2COONa towards 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5
-
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
- Wang, Ya,Mu, Shiqiang,Li, Xin,Song, Qiuling
-
supporting information
p. 1511 - 1514
(2021/09/20)
-
- Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds
-
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
-
supporting information
p. 380 - 384
(2020/10/30)
-
- Ligand-Enabled Palladium-Catalyzed Through-Space C?H Bond Activation via a Carbopalladation/1,4-Pd Migration/C?H Functionalization Sequence
-
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.
-
supporting information
p. 14075 - 14079
(2020/10/12)
-
- Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles
-
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
-
p. 6636 - 6642
(2019/03/14)
-
- 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
-
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
-
supporting information
p. 2220 - 2225
(2013/03/13)
-
- Transition metal-free direct C-H bond thiolation of 1,3,4-oxadiazoles and related heteroarenes
-
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
-
p. 11307 - 11309,3
(2020/10/15)
-
- 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
-
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
-
supporting information; experimental part
p. 471 - 474
(2012/03/08)
-
- Development of orally active nonpeptidic inhibitors of human neutrophil elastase
-
5-Amino-2-phenylpyrimidin-6-ones, some of their desamino derivatives, and miscellaneous derivatives were synthesized and biologically evaluated on both in vitro activity and oral activity in an acute hemorrhagic assay. These compounds contained an α-keto-1,3,4-oxadiazole moiety to bind covalently to the Ser-195 hydroxy group of human neutrophil elastase (HNE). Among those tested, compounds 11a-c,e,i-l(F), 11d,e,k(H), 21d,e,k(F), and 21d,e(H) showed a good oral profile. RS-Mixture 3(H) was selected for clinical evaluation based on its oral potency, duration of action, enzyme selectivity, safety profile, and ease of synthesis. Structure -activity relationships (SARs) are discussed.
- Ohmoto,Yamamoto,Okuma,Horiuchi,Imanishi,Odagaki,Kawabata,Sekioka,Hirota,Matsuoka,Nakai,Toda,Cheronis,Spruce,Gyorkos,Wieczorek
-
p. 1268 - 1285
(2007/10/03)
-
- Pesticidal pyridylthiadiazoles
-
The invention relates to pesticidal compositions which contain 2-(3-pyridyl)-1,3,4-thiadiazoles or 5-(3-pyridyl)-1,2,4-thiadiazoles of the formula STR1 wherein R1 is STR2 and each of R2 and R3 is hydrogen or C1 -C4 alkyl, to the novel compounds of the formula I themselves, to the preparation thereof, and to the use thereof in pest control.
- -
-
-
- 2-(3-Pyridyl)-1,3,4-oxadiazoles and use thereof in pest control
-
The invention relates to 2-(3-pyridyl)-1,3,4-oxadiazoles of the formula STR1 wherein R1 is hydrogen, C1 -C6 alkyl, --COOR2 or STR2 wherein R2 is C1 -C6 alkyl R3 and R4, each independently of the other, are hydrogen or C1 -C6 alkyl, X1 is hydrogen, halogen or C1 -C6 alkyl, and n is 0 or 1, to the preparation thereof, and to a method of use thereof in pest control.
- -
-
-
