33738-86-2Relevant academic research and scientific papers
Synthesis of 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed cyclization of indole-3-carbaldehyde oximes
Aksenov,Gasanova,Prokonov, F. Yu.,Aksenov,Abakarov,Aksenov
, p. 2262 - 2270 (2020/02/15)
A new method for synthesizing 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed intramolecular electrophilic amination of 2-arylindole-3-carbaldehyde O-acetyl oximes was developed.
Development, Scope, and Applications of Titanium(III)-Catalyzed Cyclizations to Aminated N-Heterocycles
Leijendekker, Leonardus H.,Weweler, Jens,Leuther, Tobias M.,Kratzert, Daniel,Streuff, Jan
supporting information, p. 3382 - 3390 (2019/02/14)
The exceptionally mild conditions of a titanium(III)-catalyzed cyclization reaction paired with a convenient acid/base extraction have enabled the straightforward synthesis, isolation, and direct N-functionalization of amino heterocycles such as 3-aminoindoles and -pyrroles. The unprotected heterocycles are ideal building blocks for the installation of aminated indoles and pyrroles into target molecules, but their sensitivity has previously impeded their synthesis by modern catalytic methods. This full paper presents the development and extended scope of the new cyclization methodology. The transformation of the products into fused bis-indoles is also demonstrated along with the discovery of an unusual palladium-catalyzed reductive biphenyl coupling reaction. The titanium(III)-catalyzed cyclization has also been applied to the synthesis of substituted 3-iminoindolines, which are of potential interest for applications in natural product synthesis and exhibit tunable blue-to-green fluorescence properties.
Unusual formation of novel highly substituted N-(3-indolyl)-imidazoles
Qu, Ji,Bhadbhade, Mohan,Kumar, Naresh,Black, David StC.
, p. 7438 - 7441 (2018/11/23)
Treatment of 3-amidoindoles with phosphoryl chloride leads to a dimerization of the resulting iminochlorides to form tetrasubstituted imidazoles in moderate yield. One indole ring undergoes ring-opening to allow the formation of the imidazole ring. This s
Catalytic Reductive Synthesis and Direct Derivatization of Unprotected Aminoindoles, Aminopyrroles, and Iminoindolines
Leijendekker, Leonardus H.,Weweler, Jens,Leuther, Tobias M.,Streuff, Jan
, p. 6103 - 6106 (2017/05/22)
A titanium(III)-catalyzed radical cyclization to unprotected 3-aminoindoles, 3-aminopyrroles, or 3-iminoindolines is reported. The reaction is non-hazardous, scalable, and allows facile isolation of the free products by extraction. The method is demonstrated on a large substrate scope and it further allows the direct installation of various nitrogen protecting groups or the synthesis of building blocks for peptide chemistry in a single sequence. Fused bisindoles can be directly accessed from the cyclization products.
Nucleophilic addition of hetaryllithium compounds to 3-Nitro-1- (phenylsulfonyl)indole: Synthesis of tetracyclic thieno[3,2-c]-δ- carbolines
Alford, Philip E.,Kishbaugh, Tara L.S.,Gribble, Gordon W.
experimental part, p. 831 - 840 (2010/09/18)
3-Nitro-1-(phenylsulfonyl)indole undergoes addition of aryl- and hetaryllithium nucleophiles to produce 2-substituted-3-nitroindoles. Mild reductive-acylation provides excellent access to 3-amido-2-hetarylindoles from which new thieno[3,2-c]-δ-carbolines
A versatile synthetic route to 11H-indolo[3,2-c]isoquinolines
Qu, Ji,Kumar, Naresh,Alamgir, Mahiuddin,Black, David StC.
scheme or table, p. 5628 - 5630 (2011/02/22)
A wide variety of indoloisoquinoline derivatives are prepared from the acid-catalyzed cyclization of 3-amido-2-phenylindoles, which in turn were obtained from the Beckmann rearrangement of 2-phenylindole-3-oximes.
