- Bromoarylation of Methyl 2-Chloroacrylate under Meerwein Conditions for the Synthesis of Substituted 3-Hydroxythiophenes
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Methyl 3-aryl-2-bromo-2-chloropropanoates can be prepared by Meerwein reaction from methyl 2-chloroacrylate and various arenediazonium salts under copper(II) bromide catalysis. The resulting readily available compounds were used as starting materials in reactions with substituted methanethiols for the construction of substituted 3-hydroxythiophenes which have not yet been accessible by other routes. Structural variety of the obtained 2-substituted 5-aryl-3-hydroxythiophenes has been achieved due to a wide range of available starting materials, including both anilines and thiols.
- Ostapiuk, Yurii V.,Shehedyn, Maksym,Barabash, Oksana V.,Demydchuk, Bohdan,Batsyts, Sviatoslav,Herzberger, Colin,Schmidt, Andreas
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p. 732 - 740
(2021/11/20)
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- A new convenient synthetic route towards 2-(hetero)aryl-substituted thieno[3,2-b]indoles using Fischer indolization
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A number of 2-(hetero)aryl-substituted thieno[3,2-b]indoles have been successfully prepared using an efficient transition-metal-free strategy, involving the Fiesselmann synthesis of methyl 5-(hetero)aryl-3-hydroxythiophene-2-carboxylates from 2-bromo-3-(hetero)arylacrylates and methyl thioglycolate, and the transformation of the synthesized 3-hydroxyesters into the corresponding thiophen-3(2H)-ones, followed by their treatment with arylhydrazines to directly form the targeted structures via Fischer indolization. At the same time, structural variety of the obtained thieno[3,2-b]indoles has been achieved due to a wide range of available starting materials, including both 2-bromo-3-(hetero)arylacrylates and arylhydrazines. In addition, two π-extended molecules, namely 1,4-bis(4H-thieno[3,2-b]indol-2-yl)benzene and 2,5-bis(4H-thieno[3,2-b]indol-2-yl)thiophene, have been synthesized in line with the current approach towards 2-(hetero)arylated thieno[3,2-b]indoles.
- Irgashev, Roman A.,Steparuk, Alexander S.,Rusinov, Gennady L.
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p. 4821 - 4832
(2018/07/15)
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- Effects of Substituents on the Chlorination of Methyl 3-Hydroxythiophene-2-carboxylate and on the Reaction of the Resulting Chlorinated Products with Active Hydrogen Containing Compounds
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The title tandem reactions that produce 5-substituted compounds of methyl 3-hydroxythiophene-2-carboxylate can also be applied with a minor modification to the 4-alkyl and 4-aryl derivatives thereof.On the other hand, 5-alkyl and 5-aryl derivatives that undergo a similar smooth chlorination behave in the second reaction in a different manner.
- Corral, Carlos,Lissavetzky, Jaime,Manzanares, Ignacio
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p. 315 - 319
(2007/10/02)
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- N-1H-tetrazol-5-yl-2-thiophene carboxamides, N-1H-tetrazol-5-yl-2-pyrrole carboxamides, N-1H-tetrazol-5-yl-2-furan carboxamides, and anti-allergic and anti-inflammatory use thereof
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The present invention is for compounds having the formula of N-1H-tetrazol-5-yl-2-thiophenecarboxamides, N-1H-tetrazol-5-yl-2-pyrrolecarboxamides, N-1H-tetrazol-5-yl-2-furancarboxamides or analogs of each of the carboxamides. The compounds are useful for the treatment of allergic or inflammatory conditions or diseases. Thus, pharmaceutical compositions and methods of use are also the invention. Processes of preparation for the compounds are also the invention.
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