Convenient Synthesis of 11‐Substituted 11<i>H</i>‐Indolo[3,2‐<i>c</i>]quinolines by Sequential Chemoselective Suzuki Reaction/Double C–N Coupling

Pham, Ngo Nghia; Janke, Sophie; Salman, Ghazwan Ali; Dang, Tuan Thanh; Le, Thanh Son; Spannenberg, Anke; Ehlers, Peter; Langer, Peter

doi:10.1002/ejoc.201700913

Cited by 17 publications

(14 citation statements)

References 44 publications

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“…In this approach, aniline was used as an amination agent, and the result was successfully obtained with up to 97% effectivity. The presence of indole and quinoline cores in a single structure enriches the library of heterocycles and helps medicinal researchers for screening purposes [65,66] …”

Section: Recent Ullman‐goldberg And/or Buchwald‐hartwig Reports In Li...mentioning

confidence: 99%

“…The presence of indole and quinoline cores in a single structure enriches the library of heterocycles and helps medicinal researchers for screening purposes. [65,66] In 2017, the Langer research group synthesized thiadiazolo-[2',3':2,3]imidazo [4,5-b]indole derivatives 38 using a two-fold Buchwald-Hartwig cyclization (Scheme 9).…”

Section: Five-membered Ring Formationmentioning

confidence: 99%

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Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles

et al. 2021

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The Carbon-Nitrogen bond formation has always been an important and useful tool in drug discovery. Its wide applications in synthesizing N-heterocycles, known as the most prevalent moiety in the active pharmacophores, have attracted increasing attention from researchers. In recent years many works were devoted to finding new and more rapid and effective chemo-and regio-selective methods for the synthesis of N-containing heterocycles. Buchwald-Hartwig and Ullman-Goldberg are two proven efficient methods for synthesizing five, six, and seven-membered heterocycles found abundantly in literature. Here, we study these two amination methods more precisely, based on the reaction conditions and the products.

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Section: Recent Ullman‐goldberg And/or Buchwald‐hartwig Reports In Li...mentioning

confidence: 99%

Section: Five-membered Ring Formationmentioning

confidence: 99%

Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles

et al. 2021

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“…The Suzuki-Miyaura reaction of 3-iodo-4-bromoquinoline (54), available by a known procedure, [24] with (2-bromophenyl)boronic acids 2a-c afforded 3-aryl-4-chloroquinolines 55a-c in excellent yields (Scheme 18). [26] The yields were much better than the yield of 52, due to less steric hindrance of position 3 of 54 in comparison to methylsubstituted quinoline 51b. The twofold Buchwald-Hartwig reaction of 55a-c gave indolo[3,2-c]quinolines 56a-k in moderate to excellent yields.…”

Section: -Iodo-4-bromoquinolinementioning

confidence: 94%

Palladium-Catalyzed Synthesis of Heterocyclic Ring Systems by Combination of Regioselective C–C with Twofold C–N Couplings

Langer

2022

Synlett

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The combination of regioselective palladium-catalyzed C–C with twofold C–N couplings allows for the synthesis of a variety of heterocyclic ring systems. Starting materials include thiophenes and benzothiophenes, pyrroles and indoles, furans and benzofurans, pyridines, quinolines and quinoxalines, complex heterocyclic systems and benzophenone derivatives. The products are in many cases complex polyheterocyclic systems, which are not readily available by other methods or, in a number of cases, were not described in the literature before. They are of pharmacological relevance or interesting in the field of material science. Products include thieno[3,2-b:4,5-b′]diindoles, thieno[3,2-b]indoles, thieno[3,4-b]indoles, 5,10-dihydroindolo[3,2-b]indoles, furo[3,2-b:4,5-b′]diindoles, benzo[4,5]furo[3,2-b]indoles, 5,7-dihydropyrido[3,2-b:5,6-b′]diindoles, 5,7-dihydropyrido[2,3-b:6,5-b´]diindoles, α-, β-, γ- and δ-carbolines, indolo[3,2-b]quinolines, indolo[2,3-b]quinolines, indolo[3,2-c]quinolines, indoloquinoxalines, pyrido[2′,1′:2,3]imidazo[4,5-b]indoles, thiadiazolo[2′,3′:2,3]imidazo[4,5-b]indoles, benzo[b]carbazolediones, acridones and thieno[3,2-b]quinolones.Contents1 Introduction2 Thiophenes and Benzothiophenes3 Pyrroles and Indoles4 Furans and Benzofurans5 Pyridines6 Quinolines and Quinoxalines7 Complex Heterocyclic Systems8 2,3-Dibromonaphthoquinone9 Benzophenone Derivatives10 Conclusions

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“…However, the applicability of those methods is often limited with regard to the preparative scope. As part of our ongoing interest in chemoselective Pd‐catalyzed reactions of quinolines and cycloisomerization reactions, we herein wish to report a new and convenient synthesis of benzoacridine and benzophenanthridine derivatives starting from dihalogenated quinolines (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzoacridines and Benzophenanthridines by Regioselective Pd‐Catalyzed Cross‐Coupling Reactions Followed by Acid‐Mediated Cycloisomerizations

et al. 2019

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A convenient synthesis of various benzoacridines and benzophenanthridines from readily available dihalogenated quinolines is reported. The synthesis is based on regioselective Suzuki and Sonogashira reactions followed by Brønsted acid‐mediated cycloisomerization. The developed methodology is highly modular and allows the construction of various ring systems and substitution patterns in high yields. The optical and electrochemical properties of selected derivatives were investigated.

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Convenient Synthesis of 11‐Substituted 11H‐Indolo[3,2‐c]quinolines by Sequential Chemoselective Suzuki Reaction/Double C–N Coupling

Cited by 17 publications

References 44 publications

Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles

Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles

Palladium-Catalyzed Synthesis of Heterocyclic Ring Systems by Combination of Regioselective C–C with Twofold C–N Couplings

Synthesis of Benzoacridines and Benzophenanthridines by Regioselective Pd‐Catalyzed Cross‐Coupling Reactions Followed by Acid‐Mediated Cycloisomerizations

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