- Combined KOH/BEt3Catalyst for Selective Deaminative Hydroboration of Aromatic Carboxamides for Construction of Luminophores
-
The selective catalytic C-N bond cleavage of amides into value-added amine products is a desirable but challenging transformation. Molecules containing iminodibenzyl motifs are prevalent in pharmaceutical molecules and functional materials. Here we established a combined KOH/BEt3 catalyst for deaminative hydroboration of acyl-iminodibenzyl derivatives, including nonheterocyclic carboxamides, to the corresponding amines. This novel transition-metal-free methodology was also applied to the construction of Clomipramine and luminophores.
- Li, Jinshan,Wang, Jiali,Yang, Jianguo,Yao, Wubing,Zhong, Aiguo
-
supporting information
p. 8086 - 8090
(2020/11/03)
-
- Efficient and regioselective synthesis of phenothiazine via ferric citrate catalyzed C-S/C-N cross-coupling
-
Efficient C-S and C-N cross-coupling reactions have been developed for regioselective, scalable and environmentally benign synthesis of substituted phenothiazine derivatives. Cross-coupling reactions were demonstrated on various challenging substrates using non-toxic, highly economical, readily available ferric citrate as a catalyst to get desired product with high regioselectivity. Atom economy is the added advantage of this protocol since additional N-protection step before coupling and eventual deprotection of the same to obtain the desired product arenot required. To the best of our knowledge, this is the first report on the use of inexpensive ferric citrate as a catalyst without involving any ligand for the synthesis of regioselectively substituted phenothiazine.
- Das, Tonmoy Chitta,Quadri, Syed Aziz Imam,Farooqui, Mazahar
-
supporting information
p. 16 - 24
(2019/05/04)
-
- Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane
-
The first hydride-catalyzed reductive cleavage of various unactivated tertiary amides, including the biologically active aryl-phenazine carboxamides and the challenging non-heterocyclic carbonyl functions, using low-cost hydrosilane as a reducing reagent has been developed. The novel catalyst system exhibits high efficiency and exclusive selectivity, providing the desired amines in useful to excellent yields under mild conditions. Overall, this transition metal-free process may offer a versatile alternative to currently employed expensive reducing reagents, high-pressure hydrogen or metal systems for the selective reductive cleavage of amides.
- Yao, Wubing,Li, Rongrong,Yang, Jianguo,Hao, Feiyue
-
p. 3874 - 3878
(2019/08/07)
-
- Transition-metal-free synthesis of phenothiazines from S-2-acetamidophenyl ethanethioate and ortho-dihaloarenes
-
An efficient cesium carbonate-mediated synthesis of phenothiazine derivatives from S-2-acetamidophenyl ethanethioates and ortho-dihaloarenes has been developed. This protocol affords an efficient approach for the construction of phenothiazine derivatives without the need of transition-metal catalyst or ligand. A plausible mechanism is proposed.
- Zhou, Yue,Zeng, Qingle,Zhang, Li
-
supporting information
p. 710 - 715
(2017/03/27)
-
- Iron catalytic phenothiazine synthetic method of compound
-
The invention provides a synthetic method of an iron-catalyzed phenothiazine compound. The synthetic method comprises the following step: in the presence of an iron salt catalyst, a ligand and an alkali, carrying out C-S coupling, C-N coupling and deacylation reaction on raw materials (N-(2-sulfydryl phenyl) acetamide and o-dibromobenzene) at a certain temperature to obtain the phenothiazine compound. The synthetic method provided by the invention is simple in operation, mild in condition, wide in application range, relatively high in yield and short in reaction time and has a good industrial prospect.
- -
-
Paragraph 0018; 0019; 0024; 0025
(2017/04/08)
-
- Method for the Synthesis of Phenothiazines via a Domino Iron-Catalyzed C-S/C-N Cross-Coupling Reaction
-
An environmentally benign and efficient method has been developed for the synthesis of phenothiazines via a tandem iron-catalyzed C-S/C-N cross-coupling reaction. Some of the issues typically encountered during the synthesis of phenothiazines in the presence of palladium and copper catalysts, including poor substrate scope, long reaction times and poor regioselectivity, have been addressed using this newly developed iron-catalyzed method.
- Hu, Weiye,Zhang, Songlin
-
p. 6128 - 6132
(2015/06/30)
-
- Synthesis of phenothiazines from cyclohexanones and 2-aminobenzenethiols under transition-metal-free conditions
-
A convenient method for the synthesis of various substituted phenothiazines from cyclohexanones and 2-aminobenzenethiols using molecular oxygen as hydrogen acceptor in the absence of transition-metals is described. For the first time cyclohexanones were used as coupling partners for the construction of phenothiazines.
- Liao, Yunfeng,Jiang, Pengcheng,Chen, Shanping,Xiao, Fuhong,Deng, Guo-Jun
-
p. 18605 - 18608
(2013/10/21)
-
- Synthesis of phenothiazines via ligand-free CuI-catalyzed cascade C-S and C-N coupling of aryl ortho-dihalides and ortho-aminobenzenethiols
-
A ligand-free CuI-catalyzed cascade C-S and C-N cross coupling of (hetero)aryl ortho-dihalides and ortho-aminobenzenethiols has been developed, and various phenothiazines were synthesized with excellent regioselectivity. A possible mechanism is proposed for the cascade coupling.
- Dai, Chuan,Sun, Xiaofei,Tu, Xingzhao,Wu, Li,Zhan, Dan,Zeng, Qingle
-
experimental part
p. 5367 - 5369
(2012/06/04)
-
- Assembly of substituted phenothiazines by a sequentially controlled CuI/L-proline-catalyzed cascade C-S and C-N bond formation
-
(Chemical equation presented) In the pro-line of fire: A general and efficient cascade reaction approach to substituted phenothiazines, which relies on controlled sequential Cul/L-prolinecatalyzed C-S and C-N bond formations, is described. DMSO = dimethylsulfoxide.
- Dawei, Ma.,Geng, Qian,Zhang, Hui,Jiang, Yongwen
-
supporting information; experimental part
p. 1291 - 1294
(2010/05/17)
-
- Synthesis of deuterium-labeled fluphenazine
-
The propylpiperazine side chain of fluphenazine has been labeled with two, four, and six deuterium atoms by lithium aluminum deuteride reduction of the appropriate ester or imide. The γ-carbon of the propyl group was labeled with two deuterium atoms by reduction of 10- (2-methoxycarbonylethyl)-2-trifluoromethyl-10H-phenothiazine, while four deuterium atoms were incorporated into the piperazine ring by reduction of 10-[3-(3,5-dioxo-1-piperazinyl)propyl]-2-trifluoro-methyl-10H-phenothiazin e. The latter reduction gave the d4-labeled N-deshydroxyethyl metabolite of fluphenazine.
- Shetty,Hawes,Midha
-
-
