cas 40312-14-9, N-HYDROXY-2-METHYL-BENZAMIDINE

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Synthesis and Biological Screening of Novel 5-(5-Aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole Derivatives
A new series of 5-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole (6a-o) have been synthesized by a cyclocondensation reaction of ethyl 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylate (3a-c) with aryl imidoxime (5a-e). The newly synthesize
Agrawal, Brijmohan R.,Farooqui, Mazahar,Khandebharad, Amol U.,Kulkarni, Pravin S.,Sarda, Swapnil R.
p. 209 - 215
(2022/01/06)

Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinones as a new series of AMPKɑ1β1γ1 activators
Adenosine monophosphate-activated protein kinase (AMPK) plays a key role in maintaining whole-body homeostasis and has been regarded as a therapeutic target for the treatment of diabetic nephropathy (DN). Herein, a series of 1,2,4-oxadiazole-containing py
Xiao, Zhihong,Peng, Yajun,Zheng, Bifeng,Chang, Qi,Guo, Yating,Chen, Zhuo,Li, Qianbin,Hu, Gaoyun
(2021/03/16)

Imidazole hydrochloride promoted synthesis of 3,5-disubstituted-1,2,4-oxadiazoles
Imidazole hydrochloride as an additive promotes the reaction of amidoximes and DMA derivatives to generated 3,5-disubstituted-1,2,4-oxadiazoles in low to excellent yields without the use of coupling reagents, oxidants, strong acids or bases and other additives.
Wang, Xuetong,Wang, Yin,Liu, Xiaoling,He, Tingshu,Li, Lingli,Wu, Huili,Zhou, Shangjun,Li, Dan,Liao, Siwei,Xu, Ping,Huang, Xing,Yuan, Jianyong
supporting information

(2021/10/14)

Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence
A simple and convenient one-pot method is reported for the synthesis of (E)-3-(3-aryl(heteroaryl, alkyl)-1,2,4-oxadiazole-5-yl)acrylic acids utilizing readily accessible or commercially available substituted benzamidoximes and inexpensive exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride. The method is based on the reaction of amidoximes with the anhydride in a basic medium at RT followed by an acid-catalyzed retro-Diels-Alder reaction. The observed stereoselective heterocyclization/retro-Diels-Alder cascade process is suitable for the synthesis of a wide range of substituted (E)-1,2,4-oxadiazole-5-ylacrylic acids featuring electron donating and electron withdrawing groups on the aryl moiety, as well as heteroaryl or alkyl substituents at position 3 of the 1,2,4-oxadiazole ring (42–79%; 15 examples).
Presnukhina, Sofia,Tarasenko, Marina,Baykov, Sergey,Smirnov, Sergey N.,Boyarskiy, Vadim P.,Shetnev, Anton,Korsakov, Mikhail K.
supporting information

(2019/12/27)

SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)
A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.
Ding, Chengrong,Ge, Shuting,Wei, Junjie,Zhang, Guofu,Zhao, Yiyong
p. 17288 - 17292
(2020/05/18)

Efficient Synthesis of Functionalized Indene Derivatives via Rh(III)-Catalyzed Cascade Reaction between Oxadiazoles and Allylic Alcohols
A highly efficient rhodium(III)-catalyzed synthesis of novel functionalized indene derivatives has been achieved via C?H activation/intramolecular aldol condensation. This cascade reaction is an atom economical protocol which could be further applied to build more complex compounds. (Figure presented.).
Zhang, Jing,Sun, Jun-Shu,Xia, Ying-Qi,Dong, Lin
supporting information
p. 2037 - 2041
(2019/03/28)

Oxadiazole Derivatives as Dual Orexin Receptor Antagonists: Synthesis, Structure–Activity Relationships, and Sleep-Promoting Properties in Rats
The orexin system plays an important role in the regulation of wakefulness. Suvorexant, a dual orexin receptor antagonist (DORA) is approved for the treatment of primary insomnia. Herein, we outline our optimization efforts toward a novel DORA. We started our investigation with rac-[3-(5-chloro-benzooxazol-2-ylamino)piperidin-1-yl]-(5-methyl-2-[1,2,3]triazol-2-ylphenyl)methanone (3), a structural hybrid of suvorexant and a piperidine-containing DORA. During the optimization, we resolved liabilities such as chemical instability, CYP3A4 inhibition, and low brain penetration potential. Furthermore, structural modification of the piperidine scaffold was essential to improve potency at the orexin 2 receptor. This work led to the identification of (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-{(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl}methanone (51), a potent, brain-penetrating DORA with in vivo efficacy similar to that of suvorexant in rats.
Brotschi, Christine,Roch, Catherine,Gatfield, John,Treiber, Alexander,Williams, Jodi T.,Sifferlen, Thierry,Heidmann, Bibia,Jenck, Francois,Bolli, Martin H.,Boss, Christoph
supporting information
p. 1257 - 1270
(2019/06/17)

A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement
A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.
Zhang, Guofu,Zhao, Yiyong,Ding, Chengrong
supporting information
p. 7684 - 7688
(2019/08/30)

Rhodium-catalyzed synthesis of 1-(acylamino)isoquinolines through direct annulative coupling of 3-aryl-1,2,4-oxadiazoles with alkynes
A Rh(III)-catalyzed direct annulative coupling of 3-aryl-1,2,4-oxadiazoles with alkynes through coordination-assisted CH activation is developed, providing a facile route to 1-(acylamino)isoquinolines. The oxadiazole ring acts as a directing group as well as an internal oxidant.
Nishii, Yuji,Bachon, Anne-Katrin,Moon, Sanghun,Bolm, Carsten,Miura, Masahiro
supporting information
p. 1347 - 1349
(2017/08/14)

Palladium-Catalyzed, Silver-Assisted Direct C-5–H Arylation of 3-Substituted 1,2,4-Oxadiazoles under Microwave Irradiation
A direct C-5–H arylation of 3-substituted 1,2,4-oxadiazoles with aryl iodides in the presence of a palladium catalyst and silver acetate is reported. This method provides a rapid, reliable way to obtain versatile 3,5-diaryl-1,2,4-oxadiazole derivatives, which are common moieties of many biologically active molecules. The synthetic applications of this novel method have been demonstrated in the concise syntheses of Ataluren and a potent RET inhibitor Yhhu251. (Figure presented.).
Li, Shan,Wan, Penghui,Ai, Jing,Sheng, Rong,Hu, Yongzhou,Hu, Youhong
supporting information
p. 772 - 778
(2017/03/11)

Base-mediated one-pot synthesis of 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride without addition of extra oxidant
A simple base-mediated one-pot synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride has been developed, in which the aldehydes act as both substrates and oxidants. The reactions include three sequential
Wang, Wei,Xu, Hao,Xu, Yuanqing,Ding, Tao,Zhang, Wenkai,Ren, Yanrong,Chang, Haibo
p. 9814 - 9822
(2016/10/31)

Facile Gold-Catalyzed Heterocyclization of Terminal Alkynes and Cyanamides Leading to Substituted 2-Amino-1,3-Oxazoles
Facile gold-catalyzed heterocyclization based upon intermolecular trapping of the generated α-oxo gold carbenes with various cyanamides R2R3NCN (R2/R3 = Alk/Alk, -(CH2)2O(CH2)2-, Ar/Ar, Ar/H) has been developed. In most cases, 2-amino-1,3-oxazoles functionalized at the nitrogen atom as well as at the fifth position of the heterocyclic ring (12 examples) were isolated in good to moderate yields.
Rassadin, Valentin A.,Boyarskiy, Vadim P.,Kukushkin
p. 3502 - 3505
(2015/07/28)

One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement
Amidoximes, obtained from the reaction of nitriles with hydroxylamine, underwent Tiemann rearrangement in the presence of benzenesulfonyl chlorides (TsCl or o-NsCl) to form the N-substituted cyanamides. Subsequently, acidic hydrolysis of the cyanamides afforded the corresponding N-monosubstituted ureas. The synthesis of N-monosubstituted ureas from nitriles was accomplished by three steps in one pot, which provides a direct access to versatile N-monosubstituted urea derivatives from a wide variety of nitriles.
Wang, Chien-Hong,Hsieh, Tsung-Han,Lin, Chia-Chi,Yeh, Wen-Hsiung,Lin, Chih-An,Chien, Tun-Cheng
supporting information
p. 1823 - 1826
(2015/08/06)

Fragmentation of GW4064 led to a highly potent partial farnesoid X receptor agonist with improved drug-like properties
Abstract The ligand activated transcription factor farnesoid X receptor (FXR) is a crucial regulator of several metabolic and inflammatory pathways and its activation by agonistic ligands seems a valuable therapeutic approach for many disorders. Most known non-steroidal FXR agonists however, have limitations that hinder their clinical development and novel FXR ligands are required. Evaluation of the co-crystal structures of the widely used FXR agonist GW4064 and related compounds in complex with the FXR ligand binding domain indicated that their disubstituted isoxazole moiety is especially relevant for FXR activation. By investigation of GW4064-fragments missing the aromatic tail, we discovered a highly potent and soluble partial FXR agonist (14, ST-1892) as well as a fluorescent FXR ligand (15) as potential pharmacological tool.
Flesch, Daniel,Gabler, Matthias,Lill, Andreas,Gomez, Roberto Carrasco,Steri, Ramona,Schneider, Gisbert,Stark, Holger,Schubert-Zsilavecz, Manfred,Merk, Daniel
p. 3490 - 3498
(2015/08/03)

Practical synthesis of N -substituted cyanamides via tiemann rearrangement of amidoximes
A facile and general synthesis of various N-substituted cyanamides was accomplished by the Tiemann rearrangement of amidoximes with benzenesulfonyl chlorides (TsCl or o-NsCl) and DIPEA.
Lin, Chia-Chi,Hsieh, Tsung-Han,Liao, Pen-Yuan,Liao, Zhen-Yuan,Chang, Chih-Wei,Shih, Yu-Chiao,Yeh, Wen-Hsiung,Chien, Tun-Cheng
supporting information
p. 892 - 895
(2014/03/21)

Antiproliferative 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides, a new tubulin inhibitor chemotype
We discovered a new chemical class of antiproliferative agents, 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides. SAR-guided optimization of the two distinct terminal fragments yielded a compound with 120 nM potency in an antiproliferative assay. Biologi
Krasavin, Mikhail,Sosnov, Andrey V.,Karapetian, Ruben,Konstantinov, Igor,Soldatkina, Olga,Godovykh, Elena,Zubkov, Fedor,Bai, Ruoli,Hamel, Ernest,Gakh, Andrei A.
p. 4477 - 4481
(2015/02/19)

AZETIDINE AMIDE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
The present invention relates to azetidine amide derivatives derivatives of formula (I) wherein rings A1 A2 and A3 are as described in the description, to pharmaceutically acceptable salts thereof, to their preparation, to
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Page/Page column 46; 47

(2014/09/29)

An experimental and theoretical study of reaction mechanisms between nitriles and hydroxylamine
The industrially relevant reaction between nitriles and hydroxylamine yielding amidoximes was studied in different molecular solvents and in ionic liquids. In industry, this procedure is carried out on the ton scale in alcohol solutions and the above transformation produces a significant amount of unexpected amide by-product, depending on the nature of the nitrile, which can cause further analytical and purification issues. Although there were earlier attempts to propose mechanisms for this transformation, the real reaction pathway is still under discussion. A new detailed reaction mechanistic explanation, based on theoretical and experimental proof, is given to augment the former mechanisms, which allowed us to find a more efficient, side-product free procedure. Interpreting the theoretical results obtained, it was shown that the application of specific imidazolium, phosphonium and quaternary ammonium based ionic liquids could decrease simultaneously the reaction time while eliminating the amide side-product, leading to the targeted product selectively. This robust and economic procedure now affords a fast, selective amide free synthesis of amidoximes.
V?r?s, Attila,Mucsi, Zoltn,Ban, Zoltn,Timri, Gza,Hermecz, Istvn,Mizsey, Pter,Finta, Zoltn
supporting information
p. 8036 - 8047
(2015/01/08)

Synthesis, insecticidal activity, and structure-activity relationship (SAR) of anthranilic diamides analogs containing oxadiazole rings
A series of anthranilic diamides analogs (3-11, 16-24) containing 1,2,4- or 1,3,4-oxadiazole rings were synthesized and characterized by 1H NMR, MS and elemental analyses. The structure of 3-bromo-N-(2-(3-(4-bromophenyl)-1, 2,4-oxadiazol-5-yl)-
Li, Yuhao,Zhu, Hongjun,Chen, Kai,Liu, Rui,Khallaf, Abdalla,Zhang, Xiangning,Ni, Jueping
supporting information
p. 3979 - 3988
(2013/07/05)

COMPOUNDS HAVING AN ETHR INHIBITING ACTIVITY - USE OF SAID COMPOUNDS AS DRUGS - PHARMACEUTICAL COMPOSITION AND PRODUCT CONTAINING SAID COMPOUNDS
The present invention relates to compounds of Formula (I), wherein R1 is chosen among the following radicals : (II); (III); (IV), (V), (VI) (VII) and n= 1 or 2 and m=1 or 2 with the proviso that m=2 when R1 is (VIII). The present invention also relates to the use thereof as drugs, more particularly in the treatment of mycobacterial infections and more particularly in the treatment of tuberculosis.
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(2013/05/21)

Formation of aromatic amidoximes with hydroxylamine using microreactor technology
In this contribution, the application of microreactor technology for amidoxime formation is demonstrated, with different aromatic nitriles reacted with a 50% solution of hydroxylamine (HA) under homogeneous conditions to reach full conversion. All reactio
Voeroes, Attila,Baan, Zoltan,Mizsey, Peter,Finta, Zoltan
p. 1717 - 1726
(2013/01/15)

Ethionamide boosters. 2. Combining bioisosteric replacement and structure-based drug design to solve pharmacokinetic issues in a series of potent 1,2,4-oxadiazole EthR inhibitors
Mycobacterial transcriptional repressor EthR controls the expression of EthA, the bacterial monooxygenase activating ethionamide, and is thus largely responsible for the low sensitivity of the human pathogen Mycobacterium tuberculosis to this antibiotic.
Flipo, Marion,Desroses, Matthieu,Lecat-Guillet, Nathalie,Villemagne, Baptiste,Blondiaux, Nicolas,Leroux, Florence,Piveteau, Catherine,Mathys, Vanessa,Flament, Marie-Pierre,Siepmann, Juergen,Villeret, Vincent,Wohlk?nig, Alexandre,Wintjens, René,Soror, Sameh H.,Christophe, Thierry,Jeon, Hee Kyoung,Locht, Camille,Brodin, Priscille,Déprez, Benoit,Baulard, Alain R.,Willand, Nicolas
experimental part
p. 68 - 83
(2012/03/10)

N-Aryl pyrrolidinonyl oxadiazoles as potent mGluR5 positive allosteric modulators
A novel series of N-aryl pyrrolidinonyl oxadiazoles were identified as mGluR5 positive allosteric modulators (PAMs). Optimization of the initial lead compound 6a led to the identification of the 12c (-) enantiomer as a potent compound with acceptable in vitro clearance, CYP, hERG and PK properties. Para substituted N-aryl pyrrolidinonyl oxadiazoles are mGluR5 PAMs while the meta and ortho substituted N-aryl pyrrolidinonyl oxadiazoles are negative allosteric modulators (NAMs). Para fluoro substitution on the N-aryl group and meta chloro or methyl substituents on the aryl oxadiazole moiety are optimal for mGluR5 PAM efficacy. The existence of an exquisitely sensitive 'PAM to NAM switch' within this chemotype making it challenging for simultaneous optimization of potency and drug-like properties.
Packiarajan, Mathivanan,Mazza Ferreira, Christine G.,Hong, Sang-Phyo,White, Andrew D.,Chandrasena, Gamini,Pu, Xiaosui,Brodbeck, Robbin M.,Robichaud, Albert J.
scheme or table
p. 5658 - 5662
(2012/09/22)

Synthesis of amidoximes using an efficient and rapid ultrasound method
This is a report on an efficient and rapid synthesis of amidoximes using ultrasound irradiation with appropriate nitrile and hydroxylamine hydrochloride in water/ethanol. This new synthetic methodology is compared with previously known methods. The main a
Barros, Carlos Jonnatan Pimentel,De Freitas, Jucleiton J. Rufino,De Oliveira, Ronaldo N.,De Freitas Filho, Jo?o R.
experimental part
p. 721 - 722
(2012/05/20)

Identification of a series of 4-[3-(quinolin-2-yl)-1,2,4-oxadiazol-5-yl] piperazinyl ureas as potent smoothened antagonist hedgehog pathway inhibitors
The Hedgehog (Hh-) signalling pathway is a key developmental pathway and there is a growing body of evidence showing that this pathway is aberrantly reactivated in a number of human tumors. Novel agents capable of inhibiting this pathway are sought, and an entirely novel series of smoothened (Smo) antagonists capable of inhibiting the pathway have been identified through uHTS screening. Extensive exploration of the scaffold identified the key functionalities necessary for potency, enabling potent nanomolar Smo antagonists like 91 and 94 to be developed. Optimization resulted in the most advanced compounds displaying low serum shift, clean off-targets profile, and moderate clearance in both rats and dogs. These compounds are valuable tools with which to probe the biology of the Hh-pathway.
Ontoria, Jesus M.,Bufi, Laura Llauger,Torrisi, Caterina,Bresciani, Alberto,Giomini, Claudia,Rowley, Michael,Serafini, Sergio,Bin, Hu,Hao, Wu,Steinkühler, Christian,Jones, Philip
scheme or table
p. 5274 - 5282
(2011/10/02)

Synthesis, mechanism of formation, and molecular orbital calculations of arylamidoximes
A simple and easy synthesis of ten arylamidoximes from arylnitriles and hydroxylamine is described. The formation of the arylamides has been observed to a much lesser extent in the present work. A new mechanism for the formation of arylamidoximes, as well
Srivastava, Rajendra M.,Pereira, Maria C.,Faustino, Wagner W. M.,Coutinho, Kaline,Dos Anjos, Janaina V.,De Melo, Sebastiao J.
experimental part
p. 1319 - 1324
(2010/05/18)

Polycyclic systems containing 1,2,4-oxadiazole ring 2*. 4-(1,2,4-Oxadiazol-5-YL)pyrrolidin-2-ones: Synthesis and prediction of biological activity
A one-pot condensation of 5-oxopyrrolidine-3-carboxylic acids, carbonyldiimidazole, and benzamidoximes leads to the formation of the novel 4-(1,2,4-oxadiazol-5-yl)pyrrolidin-2-one bicyclic systems, the structures of which have been confirmed by IR and su
Kharchenko,Detistov,Orlov
p. 600 - 605
(2013/07/11)

Non-ATP competitive glycogen synthase kinase 3β (GSK-3β) inhibitors: Study of structural requirements for thiadiazolidinone derivatives
The 2,4-disubstituted thiadiazolidinones (TDZD) were described as the first non-ATP competitive GSK-3β inhibitors. New modifications in this heterocyclic ring are here reported to study the influence on the biological activity. The basic skeleton of 1,2,4-thiadiazole and also one of the carbonyl groups are kept, while different modifications are introduced in positions 3 and 5, respectively. The GSK-3β activity of the new thiadiazole derivatives here synthesized showed IC50 values for some of the compounds in the micromolar range. Additionally, ATP competition studies have been carried out, showing that as well as the first generation of TDZD, these new compounds act in a non-competitive manner. With this study, additional requirements for the biological activity of the TDZD family have been delineated.
Castro, Ana,Encinas, Arantxa,Gil, Carmen,Braese, Stefan,Porcal, Williams,Perez, Concepcion,Moreno, Francisco J.,Martinez, Ana
p. 495 - 510
(2008/04/05)

A novel, one-pot, three-component synthesis of 1,2,4-oxadiazoles under microwave irradiation and solvent-free conditions
A novel synthesis of 3,5-disubstituted 1,2,4-oxadiazoles is described from a one-pot, three-component reaction between nitriles, hydroxylamine, and Meldrum's acids under microwave irradiation and solvent-free conditions in good to excellent yields. Georg
Adib, Mehdi,Mahdavi, Mohammad,Mahmoodi, Niusha,Pirelahi, Hooshang,Bijanzadeh, Hamid Reza
p. 1765 - 1767
(2008/02/04)

NOVEL ALKYNYL DERIVATIVES AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
The present invention relates to novel compounds of formula (I) wherein W, n, X and W’ are defined in the description; invention compounds are modulators of metabotropic glutamate receptors - subtype 5 (“mGluR5”) which are useful for the treatment of central nervous system disorders as well as other disorders modulated by mGluR5 receptors.
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(2008/06/13)

NEW COMPOUNDS
The present invention relates to new compounds of formula I, (I) a process for their preparation and new intermediates prepared therein, pharmaceutical formulations containing said compounds and to the use of said compounds in therapy.
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Page 141

(2010/02/06)

Synthesis of 3,5-disubstituted-1,2,4-oxadiazoles using tetrabutylammonium fluoride as a mild and efficient catalyst
Tetrabutylammonium fluoride (TBAF) was found to be a mild and efficient catalyst for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles. Using 0.1 - 1.0 equivalents of TBAF in THF for 1 - 24 h at room temperature, alkanoyl- and aroyloxyamidines were converted in high yield to the corresponding 3,5-disubstituted-1,2,4-oxadiazoles. A variety of R and R′ substituents were investigated.
Gangloff, Anthony R.,Litvak, Joane,Shelton, Emma J.,Sperandio, David,Wang, Vivian R.,Rice, Kenneth D.
p. 1441 - 1443
(2007/10/03)

Structure-activity relationships of acyloxyamidine cytomegalovirus DNA polymerase inhibitors
This paper describes the structure-activity relationships of a new class of cytomegalovirus DNA polymerase inhibitors having two aryl groups joined by an acyloxyamidine linker. Examination of a series of analogues in which the terminal groups are varied r
Tucker, John A.,Clayton, Terrance L.,Chidester, Connie G.,Schulz, Martin W.,Harrington, Leigh E.,Conrad, Steven J.,Yagi, Yoshihiko,Oien, Nancee L.,Yurek, David,Kuo, Ming-Shang
p. 601 - 615
(2007/10/03)

Dopamine receptor antagonists
This invention provides a novel class of oxadiazolyl piperidines which exhibit a high binding affinity for dopamine ligands. The compounds of the invention display selectivity for the dopamine D4 receptor over the dopamine D2 receptor. Preferably, these c
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(2008/06/13)

Synthesis and structure determination of N,N-diethyl-3-[3-aryl-1,2,4- oxadiazol-5-yl]propionamides
An efficient and facile synthesis of six new 1,2,4-oxadiazoles (6a-f) with a tertiary amide group attached on the side-chain, in high yield, is described. Correct assignments of side-chain methylene, methyl protons, and carbon signals have been made with the assistance of COSY, NOESY and HETCOR NMR experiments.
Srivastava, Rajendra Mohan,Da Concei??o Pereira, Maria,Hallwass, Fernando,Pacheco, Carlos R. N.
p. 2961 - 2967
(2007/10/03)

A versatile synthesis of amidines from nitriles via amidoximes
Benzamidines were prepared conveniently from benzonitriles in good yield via catalytic hydrogenation of intermediate benzamidoximes in acetic acid/acetic anhydride.
Judkins, Brian D.,Allen, David G.,Cook, Tracey A.,Evans, Brian,Sardharwala, Tsarina E.
p. 4351 - 4367
(2007/10/03)

Δ2-1,2,4-oxadiazolines by condensation of amidoximes with ketones and aldehydes
Using acetic acid as a solvent, ketones and aromatic aldehydes react with amidoximes 1 to cyclic products, Δ2-1,2,4-oxadiazolines 3. The lack of reactivity in neutral milieu is explained by MNDO calculations. Protonated carbonyl compounds are discussed to be the reactive species.
Lessel
p. 383 - 389
(2007/10/02)

3,3-Dinitrobutyl-1,2,4-oxadiazoles
The syntheses of 3,5-bis(3,3-dinitrobutyl)-1,2,4-oxadiazole and a series of 3-aryl-5-(3,3-dinitrobutyl)-1,2,4-oxadiazoles were accomplished by treating 4,4-dinitropentanoyl chloride with the appropriate amidoximes to yield the intermediate O-(4,4-dinitrop
Bjorklund, Mark D.,Coburn, Michael D.
p. 819 - 821
(2007/10/02)