19989-64-1Relevant academic research and scientific papers
Generation of a thiazole o-quinodimethane from an imino derivative and its intermolecular Diels-Alder trapping with alkynes or quinones
Jouve, Karine,Pautet, Felix,Domard, Monique,Fillion, Houda
, p. 1064 - 1067 (1999)
(E)-5-(N-Benzylformimidoyl)-4-methylthiazole 3 was prepared in good yield from 5-formyl-4-methylthiazole and benzylamine. Treatment of 3 with methylchloroformate in the presence of ethyldiisopropylamine in refluxing toluene has generated o-quinodimethane
Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines
Wu, Yue,Guo, Peng,Chen, Long,Duan, Weijie,Yang, Zengzhuan,Wang, Tao,Chen, Ting,Xiong, Fei
supporting information, p. 3271 - 3274 (2021/04/07)
The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance.
Deaminizing method for amidogen-containing aromatic compounds
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Paragraph 0021, (2016/10/09)
The invention relates to the technical field of organic synthesis, and provides a deaminizing method for amidogen-containing aromatic compounds. The deaminizing method aims at solving the problems that as for a deaminizing method commonly used at present, as strong acid is used, the environment is polluted, the reaction temperature needs to be accurately controlled and production is not facilitated. The deaminizing method for the amidogen-containing aromatic compounds includes the steps that the amidogen-containing aromatic compounds, nitrite and solvents are mixed to be put into a pressure-proof tube, a stirring reaction is carried out for 12 hours to 72 hours at the temperature of 80 DEG C to 130 DEG C, and the deaminized-amidogen aromatic compounds are separated and obtained. The deaminizing method is efficient, easy and convenient to operate and free of waste acid pollution.
FIBROSIS INHIBITOR
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, (2008/06/13)
Medicament being useful as a fibrosis inhibitor for organs or tissues, which comprises a compound of the formula (I): wherein Ring Z is optionally substituted pyrrole ring, etc.; W2 is -CO-, -SO2-, optionally substituted C1-C4 alkylene, etc.; Ar2 is optionally substituted aryl, etc.; W1 and Ar1 mean the following (1) and (2):(1) W1 is optionally substituted C1-C4 alkylene, etc.; Ar1 is optionally substituted bicyclic heteroaryl having 1 to 4 nitrogen atoms as ring-forming atoms:(2) W1 is optionally substituted C2-C5 alkylene, optionally substituted C2-C5 alkenylene, etc.; and Ar1 is aryl or monocyclic heteroaryl, which is substituted by carboxyl, alkoxycarbonyl, etc. at the ortho- or meta-position thereof with respect to the binding position of W1, or a pharmaceutically acceptable salt thereof.
Pyrrole derivatives
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, (2008/06/13)
Pyrrole derivatives represented by the following formula: wherein Ring Z is an optionally substituted pyrrole ring, etc.; W2 is —CO—, —SO2—, an optionally substituted C1-C4 alkylene, etc.; Ar2 is an optionally substituted aryl, etc.; W2 and Ar1 mean the following (1) and (2): (1) W1 is an optionally substituted C1-C4 alkylene, etc.; Ar1 is an optionally substituted bicyclic heteroaryl having 1 to 4 nitrogen atoms as ring-forming atoms: (2) W1 is an optionally substituted C2-C5 alkylene, an optionally substituted C2-C5 alkenylene, etc.; and Ar1 is an aryl or monocyclic heteroaryl, which are substituted by carboxyl, an alkoxycarbonyl, etc. at the ortho- or meta-position thereof with respect to the binding position of W1, or a pharmaceutically acceptable salt thereof These compounds are useful as medicaments such as a fibrosis inhibitor for organs or tissues.
New analogs of nitrobenzylthioinosine
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Page/Page column 29-30, (2010/11/29)
This invention relates to new analogs or derivatives of nitrobenzylthioinosine, use of these new analogs of nitrobenzylthioinosine for the treatment of pain and various other diseases as well as pharmaceuticals comprising at least on new analog of nitrobenzylthioinosine.
Generation and Diels-Alder trapping of 4,5-bis(bromomethylene)-4,5-dihydrothiazole
Jouve, Karine,Pautet, Felix,Domard, Monique,Fillion, Houda
, p. 2047 - 2050 (2007/10/03)
Treatment of 4,5-bis(dlbromomethyl)thiazole (1a) with sodium iodide in DMF led to 4,5-bis(bromomethylene)-4,5-dihydrothiazole (2a). Trapping the latter in situ with dienophiles afforded directly the aromatized cycloadducts. Starting with 5-hydroxynaphthoquinone or its 2- and 3-bromo derivatives 6 gave a mixture of the tetracyclic quinones 10 + 11 from which the 1,6-regioisomer 10 predominates. Using acrylate dienophiles gave 6-substituted benzothiazoles 13 as the major products. The regiochemistry of the cycloadditions between 2a and naphthoquinones 6 agrees with the predictions of the frontier molecular orbital theory. In contrast, the regioselectivity observed from 2a and acrylate dienophiles 12, similar to that previously obtained with 5-bromomethylene-4-methylene-4,5-dihydrothiazole (2b), is opposite to that predicted and could be better accomodated by a competitive Michael addition followed by a cyclization-elimination step.
