Synthesis of 4-substituted 3-(indol-3-yl)maleimides and azepines with annelated indole and maleimide nuclei

Lakatosh, S. A.; Luzikov, Yu. N.; Preobrazhenskaya, M. N.

doi:10.1016/j.tet.2005.06.027

Cited by 21 publications

(10 citation statements)

References 7 publications

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“…Diazepine 187.3 , containing the [1,4]diazepino[1,7- a :6,5,4- h ′ i ′]diindole framework isomeric to that found in arcyriacyanin A ( 183.4 ), was synthesized by a cyclization–aromatization sequence by Preobrazhenskaya et al (Scheme ). This strategy enabled the synthesis of substituted derivatives of 187.3 , , as well as other related ring systems, such as the benzologue 187.4 and the monoazepine isomer 187.5 . Thiourea derivatives of 187.3 showed activity as inhibitors of bacterial and human protein kinases …”

Section: Nonbenzenoid Fusionmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.

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Section: Nonbenzenoid Fusionmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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“…Indole, N-methylindole, Cu(OTf), Cu(OTf) 2 , Cu(hfacac) 2 , CuPF 6 •(CH 3 CN) 4 and Rh 2 (OAc) 4 were bought from Aldrich or Acros Chemical Company. 1-(Indol-1-yl)propan-2-ol (1c), 7 N-aminocarbonylmethylindole (1d), 8 N-acytylindole (1e), 9 tert-butyl indole-1-carboxylate (1f) 10 and aryldiazoacetates 11 were prepared according to known procedures.…”

Section: Methodsmentioning

confidence: 99%

Catalytic Reaction of Aryldiazoacetates with Indole and Its Derivatives:Profound Effect of N‐1 Substitutent on the Reaction Pathways

2008

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The reaction of indole and its derivatives with aryldiazoacetates has been studied in the presence of copper and rhodium catalysts. The electronic property of N-1 substitutent showed significant effect on the reaction pathways. The electron-donating group favored the formation of the β-alkylation products, while the electron-withdrawing group favored the formation of the cyclopropane products. A reaction mechanism was proposed based on the experimental data and previous research results. The structure of aryl group in diazo compounds also affected the yield of the β-alkylation products or the cyclopropane products.

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“…Another example of cyclization involving the α-methylene atom of the amino group was demonstrated by Preobrazhenskaya's group [74,75]. In the presence of strong acids, 2-(dialkylamino)-3-(indol-1-yl)maleimides 97 underwent cyclization to 1,4-diazepines 98 annelated to an indole ring [75,76]. Hydride ion transfer was shown [77] to be the rate-limiting step (32.9 kcal/mol) [78].…”

Section: -100%mentioning

confidence: 98%

tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

Platonova

Глухарева

Zimovets

et al. 2013

Chem Heterocycl Comp

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The term "tert-amino effect" was proposed in 1972 [1] for the cyclization reactions of tertiary anilines containing various double bonds at the ortho position. Meth-Cohn and Suschitzky [1] referred to the first observation of the tert-amino effect by Pinnow in 1895 [2]. Many different examples of reactions involving the tert-amino effect have now accumulated, and it clearly is a convenient method for the synthesis of an impressive number of nitrogen-containing heterocycles that otherwise might be difficult to obtain. Reviews were published by Reinhoudt in 1990 [3] and by Meth-Cohn in 1996 [4] on heterocyclization reactions that take place by the mechanism of the tert-amino effect. Another review dedicated to 1,6-and 1,8-naphthiridine derivatives was published in 2003 by Quintela [5]. In the review [6] that we published in 2005, attention was focused on the use of such reactions for the synthesis of spiro compounds. In the review [7], published in 2006, the cyclization reactions of ortho-vinylanilines and their heterocyclic aza analogs were considered, and classification according to the method of ring formation was proposed.

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Synthesis of 4-substituted 3-(indol-3-yl)maleimides and azepines with annelated indole and maleimide nuclei

Cited by 21 publications

References 7 publications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Catalytic Reaction of Aryldiazoacetates with Indole and Its Derivatives:Profound Effect of N‐1 Substitutent on the Reaction Pathways

tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

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