2009
DOI: 10.1002/hlca.200800423
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Highly Efficient Synthesis of Thieno[2,3‐b]indole Derivatives

Abstract: Thieno [2,3-b]indole derivatives were efficiently prepared via the reaction of 1,3-dihydro-2H-indole-2-thiones with a-bromo-substituted ketones or aldehydes and in the presence of Et 3 N (Scheme 2 and Table). The reaction took place under very mild conditions and in short times with good to excellent yields.Introduction. -Thienoindole derivatives are important target compounds because they have potential biological activities with applications in agricultural chemistry and pharmaceutical industries. So design … Show more

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Cited by 26 publications
(17 citation statements)
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“…There are few methods for the synthesis of thieno[2,3‐ b ]indoles in the literature, including deoxygenative cyclization of 2‐(2‐nitrophenyl)thiophene in refluxing triethyl phosphate, oxidative cyclization of indolin‐2‐thiones, radical or palladium‐catalyzed cyclization of 3‐(2‐bromoindol‐3yl)acrylonitriles, condensation of 3‐unsubstituted indolin‐2‐thione, intramolecular NH/CH‐coupling in benzo[ b ]thiophenes, condensation of 1‐alkylisatins and acetylated (hetero)arenes, AlCl 3 ‐catalyzed recyclization of 2‐(2‐nitrocyabatophenyl)furanes, and among others . However, all the aforementioned synthetic methods use functionalized indoles, furans, isatins and thiophenes, which require several steps to be prepared.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…There are few methods for the synthesis of thieno[2,3‐ b ]indoles in the literature, including deoxygenative cyclization of 2‐(2‐nitrophenyl)thiophene in refluxing triethyl phosphate, oxidative cyclization of indolin‐2‐thiones, radical or palladium‐catalyzed cyclization of 3‐(2‐bromoindol‐3yl)acrylonitriles, condensation of 3‐unsubstituted indolin‐2‐thione, intramolecular NH/CH‐coupling in benzo[ b ]thiophenes, condensation of 1‐alkylisatins and acetylated (hetero)arenes, AlCl 3 ‐catalyzed recyclization of 2‐(2‐nitrocyabatophenyl)furanes, and among others . However, all the aforementioned synthetic methods use functionalized indoles, furans, isatins and thiophenes, which require several steps to be prepared.…”
Section: Methodsmentioning
confidence: 99%
“…[3] The substituted thieno [2,3-b]indoles are useful for the treatment of epilepsy, neurological diseases such as Parkinson's disease and pain. [5] There are few methods for the synthesis of thieno [2,3-b]indoles in the literature, including deoxygenative cyclization of 2-(2-nitrophenyl)thiophene in refluxing triethyl phosphate, [6] oxidative cyclization of indolin-2-thiones, [7] radical or palladium-catalyzed cyc-lization of 3-(2-bromoindol-3yl)acrylonitriles, [8] condensation of 3-unsubstituted indolin-2-thione, [9] intramolecular NH/CH-coupling in benzo[b]thiophenes, [10] condensation of 1-alkylisatins and acetylated (hetero) arenes, [11] AlCl 3 -catalyzed recyclization of 2-(2-nitrocyabatophenyl)furanes, [12] and among others. [5] There are few methods for the synthesis of thieno [2,3-b]indoles in the literature, including deoxygenative cyclization of 2-(2-nitrophenyl)thiophene in refluxing triethyl phosphate, [6] oxidative cyclization of indolin-2-thiones, [7] radical or palladium-catalyzed cyc-lization of 3-(2-bromoindol-3yl)acrylonitriles, [8] condensation of 3-unsubstituted indolin-2-thione, [9] intramolecular NH/CH-coupling in benzo[b]thiophenes, [10] condensation of 1-alkylisatins and acetylated (hetero) arenes, [11] AlCl 3 -catalyzed recyclization of 2-(2-nitrocyabatophenyl)furanes, [12] and among others.…”
mentioning
confidence: 99%
“…Traditionally, thieno [2,3-b] indoles are synthesized using functionalized 2-alkynylphenylisothiocyanates, 1-alkylisatins, and indole-2-thiones as starting materials, and require several steps to afford the desired products (Scheme 1). [8][9][10] Although these classical approaches have been extensively used, there is ongoing research for new methods that have simpler work-ups, are atom-economical with good to excellent yields, use recyclable catalysts and use readily inexpensive starting materials. To date, only two reports have described the synthesis of thieno [2,3-b]indoles via a one-pot multicomponent reaction which provides a greener approach than the classical methods.…”
Section: Introductionmentioning
confidence: 99%
“…A number of synthetic routes to thieno[2,3- b ]indoles have been described in the literature, including oxidative cyclization of indolin-2-thiones 1 [ 20 ], radical or palladium catalyzed cyclization of 3-(2-bromoindol-3-yl)acrylonitriles 2 [ 21 22 ], intramolecular CH/NH-coupling in benzo[ b ]thiophenes 3 [ 23 ], AlCl 3 catalyzed recyclization of 2-(2-isothiocyanatophenyl)furanes 4 [ 24 ], reductive cyclization of 3-(2-nirtophenyl)thiophenes 5 via nitrene intermediates [ 25 – 26 ], and condensation of 3-unsubstituted indolin-2-thione 6 with aliphatic α-bromoaldehydes, α-bromoketones [ 27 ] or 3-halochromones (Hlg = Cl, Br) [ 28 ] under basic conditions ( Scheme 1 ). However, all synthetic methods mentioned above are based on using functionalized indoles, thiophenes, furans or chromone precursors, which require several steps to be prepared.…”
Section: Introductionmentioning
confidence: 99%