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Direct Synthesis of Nitrones via Transition-Metal-Free Ring-Opening of N -Tosylaziridines with the Nitrogen Atom of Various (E)-Aldoximes and (E)-Ketoximes
The KOH-, K 2 CO 3 -, or Et 3 N-catalyzed ring-opening reaction of N -tosylaziridines using the nitrogen atom of a series of (E)-aldoximes and (E)-ketoximes as a nucleophilic atom instead of an oxygen atom was developed to construct various nitrones under mild reaction conditions. Diverse (E)-aldoximes and (E)-ketoximes were demonstrated to be compatible with this reaction and the products of O -ring-opening reactions were not detected for most examples.
Chang, Honghong,Gao, Wenchao,Li, Xing,Tian, Xiuping,Wei, Wenlong,Yan, Wenjing,Zhang, Rui
p. 4043 - 4057
(2019)
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Visible-light mediated stereospecific C(sp2)-H difluoroalkylation of (Z)-aldoximes
A visible light mediated stereospecific C(sp2)-H difluoroalkylation of (Z)-aldoximes to (E)-difluoroalkylated ketoximes has been described. In this reaction, (hetero)-aromatic and aliphatic difluoroalkylated ketoximes could be obtained with the retention of the configuration of the starting aldoximes. A preliminary mechanism study showed that a difluoromethyl radicalviaan SET pathway was involved.
Chen, Hua,Deng, Hongmei,Gong, Haiying,Hao, Jian,Li, Mingjie,Peng, Yi,Wan, Wen,Wang, Qian,Zhang, Yifang
supporting information
p. 7867 - 7874
(2021/09/28)

Novel oxime derivative and application thereof in agriculture
The present invention relates to a novel oxime derivative and application thereof in agriculture. The novel oxime derivative has a structure represented by formula (I), wherein R, R, R, R and R are each independently hydrogen, fluorine, chlorine or the like, A is shown as the specification, wherein R and R are each independently hydrogen, C1-4 alkyl group, phenyl group or the like, R is C1-4 alkoxy group or the like, and R is hydrogen or C1-4 alkyl group. The novel oxime derivative disclosed by the invention is novel in structure and simple in synthesis process, and has an excellent control effect on plant diseases, particularly cucumber downy mildew.
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Paragraph 0143-0144

(2021/04/10)

Visible-Light-Mediated Strategies for the Preparation of Oxime Ethers Derived from O-H Insertions of Oximes into Aryldiazoacetates
Two visible-light-mediated O-H insertion protocols involving oximes and aryldiazoacetates leading to different products depending on the solvent employed are reported. In DCM, direct O-H insertion takes place. In THF, there is the additional incorporation of the ring-opened form of this solvent into the structure of the product. These metal-free protocols are mild and tolerant to air and moisture. The preparation of an acaricide has been developed as an example of synthetic application.
Duarte, Marcelo,Jurberg, Igor D.,Le?o, Luiz Paulo M. O.,Saito, Felipe A.,Stivanin, Mateus L.
supporting information
p. 17528 - 17532
(2021/12/02)

Enolate-Based Regioselective Anti-Beckmann C-C Bond Cleavage of Ketones
The Baeyer-Villiger or Beckmann rearrangements are established methods for the cleavage of ketone derivatives under acidic conditions, proceeding for unsymmetrical precursors selectively at the more substituted site. However, the fragmentation regioselectivity cannot be switched and fragmentation at the less-substituted terminus is so far not possible. We report here that the reaction of ketone enolates with commercial alkyl nitrites provides a direct and regioselective way of fragmenting ketones into esters and oximes or ω-hydroxyimino esters, respectively. A comprehensive study of the scope of this reaction with respect to ketone classes and alkyl nitrites is presented. Control over the site of cleavage is gained through regioselective enolate formation by various bases. Oxidation of kinetic enolates of unsymmetrical ketones leads to the otherwise unavailable "anti-Beckmann"cleavage at the less-substituted side chain, while cleavage of thermodynamic enolates of the same ketones represents an alternative to the Baeyer-Villiger oxidation or the Beckmann rearrangement under basic conditions. The method is suited for the transformation of natural products and enables access to orthogonally reactive dicarbonyl compounds.
Jahn, Ullrich,Ma?ek, Tomá?
p. 11608 - 11632
(2021/09/02)

Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?
Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.
Qiu, Xu,Wang, Yachong,Su, Lingyu,Jin, Rui,Song, Song,Qin, Qixue,Li, Junhua,Zong, Baoning,Jiao, Ning
supporting information
p. 3011 - 3016
(2021/09/13)

Visible-Light-Induced Photoaddition of N-Nitrosoalkylamines to Alkenes: One-Pot Tandem Approach to 1,2-Diamination of Alkenes from Secondary Amines
The generation of aminium radical cation species from N-nitrosoamines is disclosed for the first time through visible-light excitation at 453 nm. The developed visible-light-promoted photoaddition reaction of N-nitrosoamines to alkenes was combined with the o-NQ-catalyzed aerobic oxidation protocol of amines to telescope the direct handling of harmful N-nitroso compounds, where the desired α-amino oxime derivatives were obtained in a one-pot tandem N-nitrosation and photoaddition sequence.
Patil, Dilip V.,Si, Tengda,Kim, Hun Young,Oh, Kyungsoo
supporting information
p. 3105 - 3109
(2021/05/05)

Water mediated procedure for preparation of stereoselective oximes as inhibitors of MRCK kinase
Stereoselective aldoximes, preferably Z form have been obtained from α-cyano substituted carbonyl conjugated alkenes. This reaction occurs through Michael addition type reaction followed by retro-Knoevenagel reaction without transition-metal catalysis via C–C bond cleavage. These oximes are evaluated against cancer cell lines employing mechanistic study. Two oximes showed significant cytotoxic activity, which through in silico studies were found to inhibit MRCK Kinase, responsible for metastatic spread of cancer mortality.
Luqman, Suaib,Misra, Krishna,Pandey, Jyoti,Shrivash, Manoj Kumar,Shukla, Akhilesh Kumar,Singh, Shilipi
(2020/07/08)

Identification of morpholine based hydroxylamine analogues: Selective inhibitors of MARK4/Par-1d causing cancer cell death through apoptosis
Microtubule affinity-regulating kinase 4 (MARK4) is a serine/threonine kinase involved in the phosphorylation of MAP proteins that regulates microtubule dynamics and abets tumor progression by participating in oncogenic signaling pathways. It is overexpressed in multiple human malignancies and no drug is available for this potential therapeutic target at present. Therefore, using the structure based drug design strategy, a library of hydroxylamine derivatives of morpholine were designed and synthesized as small molecule inhibitors of MARK4. Compound 32 having the CF3 group at the ortho position of the phenyl ring tethered with the >CNOH core and the hinge binder morpholine component was found to be a potent and selective inhibitor of MARK4 over thirty other serine-threonine kinases. Study of cell viability and compound induced morphological changes in MCF-7 cancer cells discovered that molecule 32 caused death of cancerous cells through the mechanism of apoptosis. Compound 32 may be transported and delivered to the target site through the blood stream, and has promising antioxidant potential. Such bio-active molecules could serve as optimized lead candidates in drug discovery for cancer treatment through MARK4 inhibition.
Avecilla, Fernando,Azam, Amir,Gaur, Aysha,Hassan, Md. Imtaiyaz,Khan, Nashrah Sharif,Khan, Parvez,Peerzada, Mudasir Nabi
supporting information
p. 16626 - 16637
(2020/10/14)

Acetic Anhydride-Acetic Acid as a New Dehydrating Agent of Aldoximes for the Preparation of Nitriles: Preparation of 2-Cyanoglycals
Glycals, 1,2-unsatrated carbohydrates, are versatile building blocks for the synthesis of various scaffolds. Despite their potential to serve as suitable precursors in diversity-oriented synthesis, 2-cyanoglycals are less explored in terms of their synthesis and derivatization. Herein, we report a combination of Ac 2 O and AcOH as new and efficient dehydrating agent of aldoximes for the synthesis of 2-cyanoglycals. In comparison to the conventional dehydrating system of Ac 2 O-base (such as NaOH, NaOAc and K 2 CO 3), the current protocol provides superior yields and faster reaction rates. The scope and limitations of the dehydrating system are investigated.
Kinfe, Henok H.,Mabasa, Jackie,Mabasa, Tommy F.,Makhubela, Banothile C. E.,Simelane, Mthokozisi,Vatsha, Banele
supporting information
p. 991 - 996
(2020/06/10)

Annulation of Oxime-Ether Tethered Donor–Acceptor Cyclopropanes
Novel oxime-ether tethered cyclopropanes, when exposed to Yb(OTf)3 and heat, annulate to generate hydropyrrolo-oxazines products that can be taken to their respective pyrrolidines via hydrogenative N?O bond cleavage. The hydropyrrolo-oxazines are generated in a diastereoselective manner isolating the cis or trans product based on the temperature of the reaction. 20 examples of selective cis and trans hydropyrrolo-oxazines were generated in high yields by temperature control.
Irwin, Lauren C.,Allen, Meredith A.,Vriesen, Matthew R.,Kerr, Michael A.
supporting information
p. 171 - 175
(2019/12/24)

Iron-Promoted Decarboxylation of Arylacetic Acids for the Synthesis of Aromatic Nitriles with Sodium Nitrite as the Nitrogen Source
A new and effective method was developed for the synthesis of aromatic nitriles from arylacetic acids by using NaNO 2as the nitrogen source and Fe(OTf) 3as the promoter at 50 °C. A series of arylacetic acids underwent this transformation to give the targeted products in yields of 51-90%. Because of the mild conditions, the reaction is compatible with a broad range of functional groups, including ester, carboxy, hydroxy, acetamido, halo, nitro, cyano, methoxy, and even highly reactive formyl groups.
Shen, Zhenpeng,Liu, Wenbo,Tian, Xinzhe,Zhao, Zhe,Ren, Yun-Lai
supporting information
p. 1805 - 1808
(2020/11/02)

BICYCLIC KETONE COMPOUNDS AND METHODS OF USE THEREOF
The invention provides novel compounds having the general formula (I): (I) wherein R1, the A ring and the B ring are as described herein, pharmaceutical compositions including the compounds, and methods of using the compounds.
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Page/Page column 48; 49; 93; 94

(2019/02/02)

Cp?-Free Cobalt-Catalyzed C-H Activation/Annulations by Traceless N, O-Bidentate Directing Group: Access to Isoquinolines
N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp?-free cobalt-catalyzed C-H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N-O bond of the α-imino-oxy acid can serve as an internal oxidant. Terminal as well as internal alkynes can be efficiently applied to the catalytic system. This operationally simple approach shows a broad substrate scope with the products obtained in good to excellent yields.
Li, Xiao-Cai,Du, Cong,Zhang, He,Niu, Jun-Long,Song, Mao-Ping
supporting information
p. 2863 - 2866
(2019/04/17)

Synthesis and SAR of new isoxazole-triazole bis-heterocyclic compounds as analogues of natural lignans with antiparasitic activity
Despite the impressive scientific and technological advances of recent decades, no effective treatment is currently available for Chagas disease. Our research group has been studying the design and synthesis of analogues of natural lignans aiming to identify compounds with antiparasitic activity. This article reports the synthesis of 42 novel bis-heterocyclic derivatives and the structure-activity relationship study conducted based on results of biological assays against Trypanosoma cruzi amastigotes. Thirty-seven compounds were active, and eight of them had GI50 values lower than 100 μM (GI50 88.4–12.2 μM). A qualitative structure activity relationship study using three dimensional descriptors was carried out and showed a correlation between growth inhibitory potency and the presence of bulky hydrophobic groups located at rings A and D of the compounds. Compound 3-(3,4-dimethoxyphenyl)-5-((4-(4-pentylphenyl)-1H-1,2,3-triazol-1-yl)methyl)isoxazole (31) was the most active in the series (GI50 12.2 μM), showing, in vitro, low toxicity and potency similar to benznidazole (GI50 10.2 μM). These results suggest that this compound can be a promising scaffold for the design of new trypanocidal compounds.
Zimmermann, Lara A.,de Moraes, Milene H.,da Rosa, Rafael,de Melo, Eduardo B.,Paula, Fávero R.,Schenkel, Eloir P.,Steindel, Mario,Bernardes, Lílian S.C.
p. 4850 - 4862
(2018/09/11)

Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source
The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.
Yan, Yiyan,Xu, Xiaohe,Jie, Xiaokang,Cheng, Jingya,Bai, Renren,Shuai, Qi,Xie, Yuanyuan
p. 2793 - 2796
(2018/06/25)

A mild system for synthesis of aldoximes and ketoximes in the presence of N-hydroxyphthalimide in aqueous system
An efficient method for synthesis of oximes from aldehydes or ketones with N-hydroxyphthalimide or N-hydroxysuccinimide in water has been described. It is the first time to utilize NHPI as an oximation reagent to synthesize aldoximes and ketoximes from the corresponding organic carbonyl compounds without other reagents. The reaction tolerates various functional groups and affords the corresponding oximes in 76%–98% yields. The by-product phthalic acid can be recycled from the system. In addition, this method has been successfully applied to the synthesis of the precursor of some pharmacologically active amide molecules.
Jiang, Xiaoying,Xu, Xiaohe,Lin, Yuyan,Yan, Yiyan,Li, Pingping,Bai, Renren,Xie, Yuanyuan
supporting information
p. 5879 - 5885
(2018/09/06)

Depsipeptides Featuring a Neutral P1 Are Potent Inhibitors of Kallikrein-Related Peptidase 6 with On-Target Cellular Activity
Kallikrein-related peptidase 6 (KLK6) is a secreted serine protease that belongs to the family of tissue kallikreins (KLKs). Many KLKs are investigated as potential biomarkers for cancer as well as therapeutic drug targets for a number of pathologies. KLK6, in particular, has been implicated in neurodegenerative diseases and cancer, but target validation has been hampered by a lack of selective inhibitors. This work introduces a class of depsipeptidic KLK6 inhibitors, discovered via high-throughput screening, which were found to function as substrate mimics that transiently acylate the catalytic serine of KLK6. Detailed structure-activity relationship studies, aided by in silico modeling, uncovered strict structural requirements for potency, stability, and acyl-enzyme complex half-life. An optimized scaffold, DKFZ-251, demonstrated good selectivity for KLK6 compared to other KLKs, and on-target activity in a cellular assay. Moreover, DKFZ-633, an inhibitor-derived activity-based probe, could be used to pull down active endogenous KLK6.
De Vita, Elena,Schüler, Peter,Lovell, Scott,Lohbeck, Jasmin,Kullmann, Sven,Rabinovich, Eitan,Sananes, Amiram,He?ling, Bernd,Hamon, Veronique,Papo, Niv,Hess, Jochen,Tate, Edward W.,Gunkel, Nikolas,Miller, Aubry K.
supporting information
p. 8859 - 8874
(2018/10/09)

INHIBITORS OF RIP1 KINASE AND METHODS OF USE THEREOF
The invention provides novel compounds having RIP1 kinase inhibitory activity, pharmaceutical compositions including the compounds and methods of using the compounds.
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Paragraph 0518; 0519

(2018/07/04)

BICYCLIC AMIDE COMPOUNDS AND METHODS OF USE THEREOF
The invention provides novel compounds having the general formula I: wherein R1, R2, the A ring and the B ring are as described herein, pharmaceutical compositions including the compounds and methods of using the compounds.
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Paragraph 0178-0179

(2018/06/15)

Highly Chemoselective Deprotection of the 2,2,2-Trichloroethoxycarbonyl (Troc) Protecting Group
Nonreducing, pH-neutral conditions for the selective cleavage of the 2,2,2-trichloroethoxycarbonyl (Troc) protecting group are reported. Using trimethyltin hydroxide in 1,2-dichloroethane, Troc-protected alcohols, thiols, and amines can be selectively unmasked in the presence of various functionalities that are incompatible with the reducing conditions traditionally used to remove the Troc group. This mild deprotection protocol tolerates a variety of other hydrolytically sensitive and acid/base-sensitive moieties as well.
Trost, Barry M.,Kalnmals, Christopher A.,Tracy, Jacob S.,Bai, Wen-Ju
supporting information
p. 8043 - 8046
(2019/01/04)

A hydrophilic inorganic framework based on a sandwich polyoxometalate: Unusual chemoselectivity for aldehydes/ketones with in situ generated hydroxylamine
A hydrophilic inorganic porous catalyst was prepared via the hydrothermal method. The combination of [WZn3(H2O)2(ZnW9O34)2]12- and Co(ii) provides a synergistical catalytic way to promote oximation of aldehyde/ketone with in situ generated hydroxylamine that initially produces an oxime, which further either dehydrates into a nitrile or undergoes a Beckmann rearrangement to form an amide.
Xing, Songzhu,Han, Qiuxia,Shi, Zhuolin,Wang, Shugai,Yang, Peipei,Wu, Qiang,Li, Mingxue
supporting information
p. 11537 - 11541
(2017/09/18)

Novel chemoenzymatic oxidation of amines into oximes based on hydrolase-catalysed peracid formation
The efficient transformation of benzylamines into the corresponding oximes has been described by means of a chemoenzymatic process. This strategy is based on a two-step sequence developed in one-pot at 30 °C and atmospheric pressure. First, the formation of a reactive peracid intermediate occurs by means of a lipase-catalysed perhydrolysis reaction, and then this peracid acts as a chemical oxidising agent of the amines. A total of nine ketoximes were isolated in high purity after a simple extraction protocol (90-98% isolated yield), while for the eleven synthesised aldoximes a further column chromatography purification was required (71-82% isolated yield). In all cases excellent selectivities were attained, offering a practical method for amine oxidation in short reaction times (1 hour). The environmental impact of the process was analysed and compared with a recently published alternative chemical synthesis, finding for this metric a good E-factor value.
Méndez-Sánchez, Daniel,Lavandera, Iván,Gotor, Vicente,Gotor-Fernández, Vicente
p. 3196 - 3201
(2017/04/21)

Transition-Metal-Free Trifluoromethylation of Aldehyde Derivatives with Sodium Trifluoromethanesulfinate
A metal-free and cost-effective synthetic protocol for the trifluoromethylation of N,N-disubstituted hydrazones with Langlois's reagent (CF3SO2Na) to afford the corresponding functionalized trifluoromethyl ketone hydrazones has been established. It is proposed that a radical/SET mechanism proceeding via a trifluoroalkyl radical may be involved in the reaction. Applications of the methodology in industry will be found and the development of new methods for trifluoromethylation with Langlois's reagent will be continued in our laboratory.
Tan, Zheng,Zhang, Shiwei,Zhang, Yan,Li, Yunpeng,Ni, Minjie,Feng, Bainian
p. 9384 - 9399
(2017/09/23)

METHOD FOR PRODUCING ALDOXIME COMPOUND
PROBLEM TO BE SOLVED: To provide a method for producing an aldoxime compound using no expensive catalysts and reagents and also requiring no severe reaction conditions. SOLUTION: There is provided a method for producing an aldoxime compound containing a process where an aldehyde compound and an oxime compound are brought into trans oximation reaction in the presence of perchloric acid and/or the metallic salt of perchloric acid in an organic solvent and water. The metallic salt of perchloric acid is preferably ferric perchlorate, cobalt perchlorate, nickel perchlorate, zinc perchlorate, aluminum perchlorate or calcium perchlorate. Also, the organic solvent is preferably methylene chloride and/or ethylene dichloride. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0027; 0035; 0037

(2018/10/16)

M-CPBA mediated metal free, rapid oxidation of aliphatic amines to oximes
An efficient, rapid oxidation of various aliphatic amines to oximes using m-CPBA as an oxidant in ethyl acetate is described. High conversion (100%) with >90% oxime selectivity is achieved at room temperature under catalyst-free conditions. Mild reaction conditions along with an easy work up procedure offer lower byproduct formation and high selectivity for oximes in good yield and purity.
Patil, Vilas V.,Gayakwad, Eknath M.,Shankarling, Ganapati S.
p. 781 - 786
(2016/02/18)

NH2OH.HCl/BaCl2: A convenient system for synthesis of oximes from the corresponding of organic carbonyl compounds
A variety of aldehydes and ketones were converted to their corresponding oximes NH2OH·HCl/BaCl2 system in reflux conditions.
Talaei, Farhad,Setamdideh, Davood
p. 1583 - 1587
(2016/08/06)

Br?nsted acid catalyzed transoximation reaction: Synthesis of aldoximes and ketoximes without use of hydroxylamine salts
The transoximation reaction enables the transfer of an oxime to a carbonyl compound and is catalyzed by transoximase in the pupae of the silkworm. Inspired by this bio-synthetic pathway, we achieved the transoximation of oximes to aldehydes and ketones catalyzed by a Br?nsted acid under mild conditions. Hydroxylamine salt, which necessitates a stoichiometric amount of base, was not required. NMR analysis clarified that this reaction proceeded through hydroxylamines generated by the successive hydrolysis of the oxime in situ. In addition, an environmentally benign method for catalytic transoximation was demonstrated in aqueous medium on a one hundred gram scale and the reaction filtrate containing the catalyst was recovered and reused over 10 times.
Hyodo, Kengo,Togashi, Kosuke,Oishi, Naoki,Hasegawa, Genna,Uchida, Kingo
supporting information
p. 5788 - 5793
(2016/11/06)

SUBSTITUTED PYRROLIDINE COMPOUNDS
The present disclosure provides substituted pyrrolidine compounds having Formula (I): and the pharmaceutically acceptable salts and solvates thereof, wherein R1, B, X, and Z are defined as set forth in the specification. The present disclosure is also directed to the use of compounds of Formula (I) to treat a disorder responsive to the blockade of SMYD proteins such as SMYD3 or SMYD2. Compounds of the present disclosure are especially useful for treating cancer.
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Paragraph 0201

(2016/06/01)

Design, synthesis and biological evaluation of new tricyclic spiroisoxazoline derivatives as selective COX-2 inhibitors and study of their COX-2 binding modes via docking studies
A new series of 3′-(4-substitutedphenyl)-4′-(4-(methylsulfonyl)phenyl) spiroisoxazoline derivatives containing naphthalenone and chromanonespiro-bridge were synthesized for evaluation as selective cyclooxygenase-2 (COX-2) inhibitors. A synthetic reaction based on the 1,3-dipolar cycloaddition mechanism was used for the regiospecific formation of various spiroisoxazolines. One of the analogs, i.e., compound 7h, as the representative of the series was recrystallized and characterized structurally by single-crystal X-ray diffraction method. Moreover, the 3D structures of the synthesized compounds were docked into the COX-2 binding site to determine their most probable binding modes once the drug-receptor complexes are formed.
Abolhasani, Hoda,Dastmalchi, Siavoush,Hamzeh-Mivehroud, Maryam,Daraei, Bahram,Zarghi, Afshin
p. 858 - 869
(2016/04/20)

3-methyl-4-oxa-5-azahomoadamantane as an organocatalyst for the aerobic oxidation of primary amines to oximes in water
A simple and efficient catalytic system for the aerobic oxidation of primary amines into corresponding oximes has been developed, with 3-methyl-4-oxa-5-azahomoadamantane as catalyst, acetaldoxime as co-catalyst and water as solvent. This process, which uses oxygen (O2) as an economic and green oxidant and water as a green solvent, tolerates a wide range of substrates, affording the target oximes in moderate to excellent yields. It was found that high selectivity was achieved when 3-methyl-4-oxa-5-azahomoadamantane was used, and E-type oximes were the only detected products. A possible mechanism for this catalytic process is proposed.
Yu, Jiatao,Jin, Yong,Lu, Ming
supporting information
p. 1175 - 1180
(2015/04/22)

Enantioselective α-Alkylation of Benzylideneamino tert-Butyl Malonates by Phase-Transfer Catalysis
A new enantioselective synthetic method for the synthesis of α,α-dialkylmalonates with a quaternary carbon center was developed via α-alkylation of prochiral malonates by phase-transfer catalysis (PTC). Asymmetric α-alkylation of benzylideneamino tert-butyl α-methylmalonates under phase-transfer catalytic conditions in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded the corresponding α,α-dialkylmalonates in high yields (up to 97%) with excellent enantioselectivities (up to 98% ee). The products were then selectively hydrolyzed to chiral malonic monoacids under basic, acidic, or catalytic hydrogenation conditions.
Park, Cheonhyoung,Ha, Min Woo,Kim, Byungsoo,Hong, Suckchang,Kim, Doyoung,Park, Yohan,Kim, Mi-Hyun,Lee, Jae Kyun,Lee, Jeeyeon,Park, Hyeung-Geun
supporting information
p. 2841 - 2848
(2015/09/28)

An eco-friendly system for oximation of organic carbonyl compounds under microwave irradiation
The oximation of a variety of organic carbonyl compounds was efficiently carried out with NH2OH?HCl under microwave irradiation. The reactions were performed in water or water-ethanol as green solvents to give Z-aldoxime isomers from the corresponding aldehydes and E-ketoxime isomers from the corresponding ketones in a perfect selectively with excellent yields.
Batmani, Hana,Setamdideh, Davood
p. 699 - 703
(2015/01/16)

A novel and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to oximes
A simple and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to corresponding oximes by using toluene as the solvent is described. This practical method can use O2 as the economic and green oxidant, tolerate a wide range of substrates, which can afford the target oximes in moderate to excellent yields.
Yu, Jiatao,Cao, Xiaohua,Lu, Ming
supporting information
p. 5751 - 5755
(2015/02/02)

One-pot two-step sequential transformation: Highly efficient construction of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers
A practical variety of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers bearing broad functional groups were synthesized in moderate to good yields. The key highlight of this disclosure involving a one-pot two-step tandem procedure in aqueous media: the in situ formation of aryl aldehydes or ketones oximes followed by the SNAr reaction with pentafluorobenzonitrile via the high selective CF bond cleavage.
Liu, Cuibo,Yin, Xuguang,Chang, Jing,Tang, Xiangyang,Zhang, Bin
p. 101 - 108
(2014/08/18)

Design, synthesis and in vitro cytotoxicity evaluation of new 3',4'-bis (3,4,5-trisubstituted)-4'H-spiro[indene-2,5'-isoxazol]-1(3H)-one derivatives as promising anticancer agents
A new series of 3',4'-bis(3,4,5-trimethoxyphenyl)-4'H-spiro[indene-2,5'-isoxazol]-1(3H)-one derivatives was designed and synthesized. The cytotoxic effects of the synthesized compounds were evaluated on several different human cancer cells. Among them, compound 9e displayed the most potent in vitro antiproliferative activity with IC50 values of 0.07±0.01 μM on T47D cells. Another potent derivative 9h displayed an IC50 value of 0.12±0.07 μM against T47D cells, comparable to that of the positive controls (Colchicine' Cisplatin' Vincristine' Vinblastine' Doxorubicin' Celecoxib). The structure-activity relationships were discussed and both anti-tubulin and COX-2 inhibitory effects were proposed for the developed compounds
Abolhasani, Hoda,Zarghi, Afshin,Abolhasani, Ahmad,Hamzeh-Mivehroud, Maryam,Bargahi, Nasrin,Notash, Behrouz,Mojarrad, Javid Shahbazi,Dastmalchi, Siavoush
p. 1149 - 1161
(2015/03/31)

New approach to oximes through reduction of nitro compounds enabled by visible light photoredox catalysis
A range of nitro compounds are smoothly reduced to their corresponding oximes under the synergistic effects of visible light irradiation, the Ru(bpy)3Cl2 photocatalyst, Hünig's base, Mg(ClO 4)2 activation, and MeCN solvent. This remarkably mild and environmentally benign protocol, when orchestrated with classical Beckmann rearrangement, enables such high-value industrial feedstock as caprolactam to be readily accessed from simple precursor nitrocyclohexane.
Cai, Shunyou,Zhang, Shaolong,Zhao, Yaohong,Wang, David Zhigang
supporting information
p. 2660 - 2663
(2013/07/11)

Synthesis of oximes with NH2OH.HCl/DOWEX(R)50WX4 system
The oximation of a variety of carbonyl compounds was efficiently carried out with DOWEX(R)50WX4/NH2OH·HCl system. The reactions were performed in ethanol to give Z-aldoximation isomers of aldehydes and E-oximaton of acetophenone derivatives in a perfect selectively. The oximation of compounds with two carbonyl groups was carried out selectively on one carbonyl moiety. Also, the oximation of aldehydes over ketones has been accomplished successfully by this system.
Setamdideh, Davood,Khezri, Behrooz,Esmaeilzadeh, Seyran
p. 1119 - 1124
(2012/10/30)

A facile steroselective synthesis of Z-aldoximes from benzaldehyde and hydroxlaminehydrochloride in dry media
The synthesis of Z-arylaldoximes has been carried out under microwave conditions using CdSO4 as catalyst. The yields obtained were in the range 84-88%.
Dewan, Sharwan K.,Meenakshi
p. 1531 - 1532
(2013/02/23)

Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction
A highly stereoselective synthesis of E-isomer of aldoximes was developed through a basecatalysed domino aza-Michael/retro-Michael reaction of hydroxylamine and 2-(R-benzylidene)malononitrile. This reaction generates (E)-aldoxime diastereomer in high yields (eight examples, isolated yields of 82-93 %), excellent diastereomeric purity (diastereomeric ratio higher than 95 : 5 by 1H NMR), and proceeds under mild reaction conditions (aqueous NaOH, pH 12, room temperature, 4 h).
Chen, Wei,Yu, Wei-Guo,Shi, Hai-Bo,Lu, Xiao-Yan
experimental part
p. 308 - 311
(2012/08/28)

Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction
A highly stereoselective synthesis of E-isomer of aldoximes was developed through a base-catalysed domino aza-Michael/retro-Michael reaction of hydroxylamine and 2-(R-benzylidene)malononitrile. This reaction generates (E)-aldoxime diastereomer in high yie
Chen, Wei,Yu, Wei-Guo,Shi, Hai-Bo,Lu, Xiao-Yan
p. 308 - 311
(2015/03/04)

Electrochemical tandem synthesis of oximes from alcohols using KNO 3 as the nitrogen source, mediated by tin microspheres in aqueous medium
Electrochemical oximation of alcohols was realized with KNO3 as the nitrogen source mediated by tin microspheres.
Zhang, Li,Chen, He,Zha, Zhenggen,Wang, Zhiyong
supporting information; experimental part
p. 6574 - 6576
(2012/07/30)

Microwave-promoted one-pot conversion of alcohols to oximes using 1-methylimidazolium nitrate, [Hmim][NO3], as a green promoter and medium
A wide variety of oximes were prepared from different types of alcohols with hydroxylamine hydrochloride using 1-methylimidaziloum nitrate, [Hmim][NO3], ionic liquid as a reaction medium and promoter under microwave irradiation. This protocol provides a one-pot oxime synthesis with high yields that is facile, eco-friendly and the ionic liquid can be recovered and reused.
Mirjafari, Arsalan,Mobarrez, Niloufar,O'Brien, Richard A.,Davis Jr, James H.,Noei, Jalil
experimental part
p. 1065 - 1070
(2012/03/11)

Simple, efficient and green synthesis of oximes under ultrasound irradiation
The condensation of aldehydes andketones with hydroxylamine hydrochloride gives oximes in 81-95%yields in water andEtOH under ultrasound irradiation. Compared to conventional methods, the main advantages of the present procedure are milder reaction conditions, shorter reaction times and higher yields.
Khoramabadi-Zad,Azadmanesh,Rezaee
p. 192 - 194
(2013/01/09)

Studies of nitrile oxide cycloadditions, and the phenolic oxidative coupling of vanillin aldoxime by Geobacillus sp. DDS012 from Italian rye grass silage
During studies directed towards the discovery of nitrile hydrolysing enzymes from thermophiles, vanillin aldoxime was incubated with the thermophilic organism, Geobacillus sp. DDS012 isolated from Italian rye grass (Lolium multiflorum) silage. The predominant product was a dihydro-dimer, which could only be characterised by LC-MS. This was initially imagined to be the product of cycloaddition of vanillin aldoxime with the corresponding nitrile oxide, but preparation of the supposed adduct and model studies excluded this possibility. The rate constant for the second order dimerisation of 4-O-acetyl vanillin nitrile oxide was measured (1.21 × 10-4 M-1 s -1, 0.413 M, 25 °C) and the 13C-NMR signal for the nitrile oxide carbon was observed (δC 34.4, br. t 1J13C,14N circa 50 Hz). Treatment of vanillin aldoxime with potassium persulfate and iron sulfate gave material with the same LC-MS properties as the natural product, which is therefore identified as 5,5′-dehydro-di-(vanillin aldoxime) 1d formed by phenolic oxidative coupling. This journal is The Royal Society of Chemistry.
Kelly, David R.,Baker, Simon C.,King, David S.,De Silva, Deepa S.,Lord, Gwyn,Taylor, Jason P.
p. XX787-796
(2008/09/17)

Enantioselective Strecker-type reaction of phosphinoyl ketimines catalyzed by a chiral Zr-bipyridyldiol catalyst
An enantioselective Strecker reaction of N-diphenylphosphinoyl ketimines with TMSCN employing a chiral zirconium complex formed from chiral bipyridyl diol 1 as catalyst is described. The catalytic efficiency of chiral ligand 1 with other Lewis acids was also explored. Higher yields (50-85%) with moderate to good enantioselectivities (30-80%) were achieved for a variety of N-diphenylphosphinoyl ketimines.
Chen, Yi-Jing,Chen, Chinpiao
experimental part
p. 2201 - 2209
(2009/04/05)

Novel oxidative nitrogen to carbon rearrangement found in the conversion of anilines to benzaldoximes by treating with HCHO/H2O2
Novel rearrangement was found by reacting anilines with HCHO/H2O2 resulting in the synthesis of various benzaldoximes. The mechanism of the rearrangement is proposed and suggested that the rearrangement might proceed via unstable N-phenyloxazirane intermediate followed by the transfer of aryl moiety from nitrogen to carbon atom leading to the formation of benzaldoxime.
Kapuriya, Naval,Kapuriya, Kalpana,Dodia, Narsinh M.,Lin, Yi-Wen,Kakadiya, Rajesh,Wu, Chao-Ting,Chen, Ching-Huang,Naliapara, Yogesh,Su, Tsann-Long
p. 2886 - 2890
(2008/09/21)

Iridium-catalyzed conversion of alcohols into amides via oximes
(Chemical Equation Presented) The iridium catalyst [Ir(Cp*)Cl 2]2 is effective for the rearrangement of oximes to furnish amides. The reaction has been combined with catalytic transfer hydrogenation between an alcohol and alkene to allow the conversion of alcohols into amides in a one-pot process.
Owston, Nathan A.,Parker, Alexandra J.,Williams, Jonathan M. J.
p. 73 - 75
(2007/10/03)

Highly efficient ruthenium-catalyzed oxime to amide rearrangement
A wide range of aldoximes has been converted into the corresponding amides using the ruthenium-based catalyst Ru(PPh3)3(CO)H 2/dppe/ TsOH. The amides are generated in high yield and selectivity, with catalyst loading as low as 0.04 mol %.
Owston, Nathan A.,Parker, Alexandra J.,Williams, Jonathan M. J.
p. 3599 - 3601
(2008/02/12)

Synthesis of [2,3,4,5,6-2H5]phenyl glucosinolate
Starting from commercially available [2,3,4,5,6-2H 5]benzoic acid, [2,3,4,5,6-2H5]phenyl glucosinolate was synthesized. Under negative-ion electrospray-ionization mass spectrometric conditions, this compound affords a peak at m/z 399. Since this m/z value is not known from the ions derived from natural glucosinolates, the [2,3,4,5,6-2H5]phenyl glucosinolate reported here is useful as an internal standard for the quantification of glucosinolates by negative-ion mass spectrometry (MS) and liquid chromatography (LC)/MS techniques. Copyright
Bialecki, Jason B.,Ruzicka, Josef,Attygalle, Athula B.
p. 711 - 715
(2008/02/11)