5922-60-1Relevant articles and documents
A PROCESS FOR THE SYNTHESIS ANTHRANILIC DIAMIDE COMPOUNDS AND INTERMEDIATES THEREOF
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Page/Page column 25; 26, (2020/09/08)
The present invention disclosed a process for the synthesis of anthranilic diamide compound of formula (I), wherein, R1, R2, R3a, R3b, R3c, R4, R5, R6 and Z are as defined in the detailed description. The process comprising the step of obtaining a mono- or dicyano substituted aniline compound of formula (IV) which is then converted to an anthranilic acid compound of formula (V) or an anthranilic amide compound of formula (Va). Further, the compound of formula (VI) can be optionally synthesized from compound of formula (IV or V or Va).
High Performance and Active Sites of a Ceria-Supported Palladium Catalyst for Solvent-Free Chemoselective Hydrogenation of Nitroarenes
Shi, Xiuxiu,Wang, Xueguang,Shang, Xingfu,Zou, Xiujing,Ding, Weizhong,Lu, Xionggang
, p. 3743 - 3751 (2017/10/16)
Cerium oxide-supported palladium catalysts (Pd/CeO2) prepared by a simple impregnation method exhibit exciting catalytic activity and high chemoselectivity for the solvent-free hydrogenation of a variety of substituted nitroarenes including the reducible functional groups to the corresponding aromatic amines under mild reaction conditions. Taking nitrobenzene as an example, the Pd/CeO2 catalyst can afford aniline yields of >99 % with turnover frequencies as high as 11 411 h?1 and 69 824 h?1 at 40 °C and 100 °C, respectively. Pd2+ ion species exist as isolated single atoms with ?Pd2+?O2??Ce4+? linkages on the surface of PdxCe1?xO2?σ solid solution and are found to be active sites for the selective hydrogenation of nitroarenes in the absence of solvent. The superior catalytic performance can be attributed to the cooperative effect between Pd2+ ions and unique surface sites of CeO2. A possible mechanism is proposed for the hydrogenation of nitroarenes with H2 over the Pd/CeO2. The Pd/CeO2 catalyst can be recovered easily and reused for at least seven recycling reactions without loss of catalytic properties.
Microwave-assisted protection of primary amines as 2,5-dimethylpyrroles and their orthogonal deprotection
Walia, Amit,Kang, Soosung,Silverman, Richard B
, p. 10931 - 10937 (2013/11/19)
Primary amines can be readily doubly protected as N-substituted 2,5-dimethylpyrroles. Although this protecting group is stable toward strong bases and nucleophiles, long reaction times are required for both the protection and deprotection steps, generally resulting in low deprotection yields. By employing microwave irradiation, protection and deprotection reaction times are dramatically reduced. Furthermore, deprotection with dilute hydrochloric acid in ethanol increases reaction yields. Diverse deprotection conditions have been developed in conjunction with microwave irradiation, so that protection as an N-substituted 2,5-dimethylpyrrole can be orthogonal to other standard amine protecting groups, such as tert-butyloxycarbonyl (Boc), carbobenzyloxy (Cbz), and 9-fluorenylmethyloxycarbonyl (Fmoc).
Synthesis of benzotriazine and aryltriazene derivatives starting from 2-azidobenzonitrile derivatives
Nakhai, Azadeh,Stensland, Birgitta,Svensson, Per H.,Bergman, Jan
experimental part, p. 6588 - 6599 (2011/02/26)
3-Substituted 3,4-dihydro-4-imino-1,2,3-benzotriazine derivatives 7 were formed from 2-azidobenzonitriles 4 as starting materials on treatment with Grignard or lithium organic reagents. In some cases these procedures gave aryltriazenes 10 and 11 as products. All compounds were identified by NMR spectroscopy and the structures of three products, namely 7a, 10a and 11i, were corroborated by X-ray crystallography. The reactions of 2-azidobenzonitrile derivatives with Grignard reagents have been investigated. These reactions, depending on the type of Grignard reagent and the substituents on the 2-azidobenzonitrile derivatives, resulted in benzotriazines and triazenes. Copyright
The conversion of 2-(4-chloro-5H-1,2,3-dithiazolylideneamino)benzonitriles into 3-aminoindole-2-carbonitriles using triphenylphosphine
Michaelidou, Sophia S.,Koutentis, Panayiotis A.
experimental part, p. 8428 - 8433 (2009/12/26)
2-(4-Chloro-5H-1,2,3-dithiazolylideneamino)benzonitrile 1a reacts with triphenylphosphine (4 equiv) in the presence of water (2 equiv) to afford anthranilonitrile 2a, 3-aminoindole-2-carbonitrile 3a and (2-cyanoindol-3-yl)iminotriphenylphosphorane 4a, tog
Synthesis of 2-amino-5-chlorobenzonitrile
Mahajan,Mahalakshmi
, p. 1299 - 1300 (2007/10/03)
Synthesis of 2-amino-5-chlorobenzonitrile by using cheaper and easily available raw materials is discussed.
Acetonitrile-mediated synthesis of 2,4-dichloroquinoline from 2-ethynylaniline and 2,4-dichloroquinazoline from anthranilonitrile
Lee, Jae Hak,Lee, Byoung Se,Shin, Hyunik,Nam, Do Hyun,Chi, Dae Yoon
, p. 65 - 68 (2007/10/03)
2,4-Dichloroquinolines and 2,4-dichloroquinazolines were synthesized from 2-ethynylanilines and anthranilonitriles, respectively, using diphosgene in acetonitrile and heating at 130 °C or 150 °C for 12 hours. This reaction was applied to the synthesis of 4,6-dichloropyrazolo[3,4-d]pyrimidine (dichloro-9H-isopurine). The postulated mechanism is also described. Georg Thieme Verlag Stuttgart.
Practical and efficient chlorination of deactivated anilines and anilides with NCS in 2-propanol
Zanka, Atsuhiko,Kubota, Ariyoshi
, p. 1984 - 1986 (2007/10/03)
Deactivated anilines and anilides were efficiently monochlorinated with NCS in 2-propanol. The described method was applicable to a large scale synthesis.
Quinolone derivatives
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, (2008/06/13)
A class of 2-(1H)-quinolone derivatives, substituted at the 3-position by an optionally substituted aryl substituent, are selective non-competitive antagonists of NMDA receptors and/or are antagonists of AMPA receptors, and are therefore of utility in the treatment of conditions, such as neurodegenerative disorders, convulsions or schizophrenia, which require the administration of an NMDA and/or AMPA receptor antagonist.
Chiral resolution process
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, (2008/06/13)
A chiral resolution process is described for the purification of a substituted chiral quinazoline, by salt formation with a resolving agent, followed by crystallization.
