15826-91-2Relevant articles and documents
One-Pot Tandem Access to Phenothiazine Derivatives from Acetanilide and 2-Bromothiophenol via Rhodium-Catalyzed C-H Thiolation and Copper-Catalyzed C-N Amination
Rui, Xiyan,Wang, Chao,Si, Dongjuan,Hui, Xuechao,Li, Keting,Wen, Hongmei,Li, Wei,Liu, Jian
, p. 6622 - 6632 (2021)
A one-pot and step economic reaction involving Rh(III)-catalyzed C-H thiolation and relay Cu(II)-catalyzed C-N amination of acetanilide and 2-bromothiophenol is reported here, with several valuable phenothiazine products obtained. This synthesis protocol proceeds from easily starting materials, demonstrating high atom economy, broad substrate scope, and good yield. Furthermore, the directing group can be easily eliminated, and chlorpromazine is provided in a large scale; thus this synthesis protocol could be utilized to construct phenothiazine scaffolds.
RUTHENIUM-CATALYSED REARRANGEMENTS OF AZOBENZENES IV. REARRANGEMENTS OF DEUTERATED AZOBENZENES TO 1-PHENYLBENZIMIDAZOLE AND N-PHENYL-1,2-PHENYLENEDIAMINE DERIVATIVES
Spencer, Alwyn
, p. 199 - 210 (1985)
The ruthenium-catalysed reactions of azobenzene-d10 and 4,4'-disubstituted azobenzene-d8 compounds with non-deuterated tri-n-butylamine, n-butanol or 2-propanol give 1-phenylbenzimidazole or N-phenyl-1,2-phenylenediamine derivatives.The distibution of 1H in the aromatic rings of these products and in the recovered azobenzenes indicated that in all cases ortho-metallation of the azobenzene derivative has occured.The significance of those and other observations for the mechanism of these reactions is discussed.
Hydrogen/deuterium exchange on aromatic rings during atmospheric pressure chemical ionization mass spectrometry
Davies, Noel W.,Smith, Jason A.,Molesworth, Peter P.,Ross, John J.
, p. 1105 - 1110 (2010)
It has been demonstrated that substituted indoles fully labelled with deuterium on the aromatic ring can undergo substantial exchange back to partial and even fully protonated forms during atmos-pheric pressure chemical ionisation (APCI) liquid chromatography/mass spectrometry (LC/MS). The degree of this exchange was strongly dependent on the absolute quantity of analyte, the APCI desolvation temperature, the nature of the mobile phase, the mobile phase flow rate and the instrument used. Hydrogen/deuterium (H/D) exchange on several other aromatic ring systems during APCI LC/MS was either undetectable (nitrobenzene, aniline) or extremely small (acetanilide) compared to the effect observed for substituted indoles. This observation has major implications for quantitative assays using deuterium-labelled internal standards and for the detection of deuter-ium-labelled products from isotopically labelled feeding experiments where there is a risk of back exchange to the protonated form during the analysis.
Stable isotope labeled sulfamethoxazole and synthesis method thereof
-
Paragraph 0035; 0039; 0045; 0047, (2019/07/29)
The invention discloses stable isotope labeled sulfamethoxazole and a synthesis method thereof. The synthesis method comprises following steps: S1, stable isotope labeled aniline and acetic anhydrideare subjected to a reaction, and stable isotope labeled acetaminobenzene is prepared; S2, stable isotope labeled acetaminobenzene and chlorosulfonic acid are subjected to a reaction, and stable isotope labeled p-acetamidobenzene sulfonyl chloride is prepared; S3, stable isotope labeled p-acetamidobenzene sulfonyl, 3-amino-5-methylisoxazole and 4-dimethylaminopyridine are subjected to a reaction, and stable isotope labeled acetylsulfamethoxazole is prepared; S4, stable isotope labeled acetylsulfamethoxazole is hydrolyzed under the alkaline condition, and stable isotope labeled sulfamethoxazoleis obtained. The synthesis process is simple, a product is easy to separate and purify, chemical purity and isotope abundance of the obtained product both reach 99% or higher, and the product meets the requirement of a standard reagent for quantitatively detecting sulfamethoxazole; stable isotope labeled sulfamethoxazole has high use value and good economic efficiency.
Stable isotope-labeled sulfadimidine and synthesis method thereof (by machine translation)
-
Paragraph 0032; 0037-0039; 0044; 0046, (2019/08/01)
The invention discloses a stable isotope-labeled sulfadimidine and a synthesis method. S1: The stable isotope-labeled acetaminophthic acid chloride; S2: the stable isotope-labeled p-acetyl aminobenzyl chloride is prepared; and the stable isotope-labeled p-acetyl aminobenzyl chloride is reacted, 2 -dimethyl -4 -5 - 6 -bromopyrimidine, and the like. S3 is obtained by reacting the stable isotope-labeled acetaminophthyl chloride with chlorosulfonic acid. The formed intermediate is hydrolyzed under basic conditions to prepare a stable isotope-labeled sulfadimidine. Compared with the prior art, the method has the advantages of mild conditions, simple process, short process route, easy separation and purification of products, high yield, high chemical purity and stable isotope abundance of 99% the obtained products, and high use value, and can be used as a standard reagent for quantitatively detecting sulfadimethoxuracil; and the method has good economical. (by machine translation)
H-D Exchange Deuteration of Arenes at Room Temperature
Sawama, Yoshinari,Nakano, Akihiro,Matsuda, Takumi,Kawajiri, Takahiro,Yamada, Tsuyoshi,Sajiki, Hironao
supporting information, p. 648 - 653 (2019/02/14)
Arene nuclei efficiently underwent the hydrogen (H)-deuterium (D) exchange reaction catalyzed by platinum group metals on carbon in a mixed solvent of 2-propanol and D2O at room temperature to produce deuterium-labeled arenes. Platinum on carbon (Pt/C) and iridium on carbon (Ir/C) were applicable catalysts, and the various arenes bearing a carbonyl group, fluorine, phenolic hydroxy group, amino group, or phosphonic acid on the aromatic nucleus were effectively deuterated. Nonheating conditions are valuable for the scalable industrial preparation.
Stable isotope deuterium labeled sulfanilamide drug and preparation method thereof
-
Paragraph 0026; 0033; 0034; 0035, (2018/04/26)
The invention belongs to the technical field of chemical synthesis, and specifically relates to a stable isotope deuterium labeled sulfanilamide drug and a preparation method thereof. The preparationmethod comprises the following steps: (1) subjecting benzene-d6 (I) to a nitratlon reaction so as to prepare deuterium labeled nitrobenzene-d5 (II); (2) reducing nitro of the deuterium labeled nitrobenzene-d5 (II) so as to prepare deuterium labeled aniline-d5 (III); (3) under the conditions of anhydrous sodium acetate and glacial acetic acid, subjecting the deuterium labeled aniline-d5 (III) and acetic anhydride to a reaction so as to prepare deuterium labeled N-acetanilide-d5 (IV); (4) subjecting the deuterium labeled N-acetanilide-d5 (IV) and chlorosulfonic acid to a reaction so as to prepare deuterium labeled 1-chlorosulfonyl-4-acetamidobenzene-d4 (V); and (5) allowing R to substitute chlorine of the deuterium labeled 1-chlorosulfonyl-4-acetamidobenzene-d4 (V), and carrying out hydrolysis so as to prepare an isotope deuterium labeled sulfanilamide drug (VII). The preparation method provided by the invention has the advantages of simple reaction conditions, short reaction time, highconversion efficiency, strong economy, and applicability to mass synthesis.
Visible-Light-Promoted C-H Arylation by Merging Palladium Catalysis with Organic Photoredox Catalysis
Jiang, Jian,Zhang, Wen-Man,Dai, Jian-Jun,Xu, Jun,Xu, Hua-Jian
, p. 3622 - 3630 (2017/04/11)
The use of a dual palladium/organic photoredox catalytic system enables the directed arylation of arenes with aryldiazonium salts with a broad substrate scope at room temperature under mild reaction conditions. This study thus serves as not only an alternative route for the biaryl motifs but also a new example for the application of an organic photoredox catalyst.
Pd-catalyzed dehydrogenative aryl-aryl bond formation via double C(sp2)-H bond activation: Efficient synthesis of [3,4]-fused oxindoles
Bunescu, Ala,Piou, Tiffany,Wang, Qian,Zhu, Jieping
supporting information, p. 334 - 337 (2015/03/03)
A Pd(0)-catalyzed double cyclization of easily available o-bromoanilides leading to strained [3,4]-fused oxindoles was developed. The reaction proceeded through a highly ordered sequence involving key carbopalladation, 1,4-Pd migration, and C(sp2)-H functionalization steps. (Chemical Equation Presented).
Phenylene ring motions in isomeric glassy epoxy networks and their contributions to thermal and mechanical properties
Tu, Jianwei,Tucker, Samuel J.,Christensen, Stephen,Sayed, Abdelwahed R.,Jarrett, William L.,Wiggins, Jeffrey S.
, p. 1748 - 1758 (2015/03/31)
Cross-linked epoxies prepared from diglycidyl ether of bisphenol A (DGEBA) exhibit substantial property differences due to isomeric structures of the diamine curatives, 3,3′- and 4,4′-diaminodiphenyl sulfone (DDS). Here, the motions of phenylene rings on both the bisphenol A (BPA) and DDS structures of the networks were investigated through solid-state NMR 2H line shape analysis to trace the molecular origins. Ring deuterated monomers, namely, DGEBA-d8, 33DDS-d8, and 44DDS-d8, were synthesized, and four deuterated networks were prepared. The line shapes of the ring motions were interpreted using a motional model that described both ring π-flips and main-chain fluctuations. The contributions of different ring motions to mechanical relaxations are elucidated, and the molecular origins of property differences are identified.
