Synthesis of Triazole-Fused Phenanthridines through Pd-Catalyzed Intramolecular Phenyl C–H Activation of 1,5-Diaryl-1,2,3-triazoles

Wang, Jiazhuang; Yang, Jianhua; Fu, Xuxin; Qin, Guiping; Xiao, Tiebo; Jiang, Yubo

doi:10.1055/s-0037-1611859

Cited by 11 publications

(3 citation statements)

References 6 publications

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“…Fu and co‐workers published a procedure for the decarboxylative aromatic iodination (Scheme ) . They used Ir(dF(CF 3 )ppy) 2 (dtbbpy)(PF 6 ) as the commercially available photocatalyst, N ‐iodosuccinimde (NIS) in combination with I 2 as iodine source and cesium carbonate as a base.…”

Section: Methodsmentioning

confidence: 99%

A Retrosynthetic Approach for Photocatalysis

et al. 2020

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Visible‐light‐mediated chemical reactions have become very popular within the last 15 years. Many excellent reviews have summarized reaction principles and recent results in photochemistry and photocatalysis. However, despite their popularity photochemistry and photoredox catalysis are not regular parts of the bachelor and master curriculum of chemistry education. As a consequence, most chemists will use in synthesis planning classic retrosynthetic disconnections and only rarely consider photocatalytic steps. The aim of this article is to be a useful tool for synthetic chemists, that are interested in the synthetic aspects of photocatalysis and looking for a specific retrosynthetic disconnection. Not only are informative schemes provided but also are the availability of the catalysts and reagents as well as the functional group tolerance of the respective method briefly discussed.

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Section: Methodsmentioning

confidence: 99%

A Retrosynthetic Approach for Photocatalysis

et al. 2020

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“…In 2013, Shi et al [ 62 ] designed 4-( ortho -halo-aryl) 1,2,3-triazoles to merge with activated nitriles, forming a series of 5-amino-[1,2,3]triazolo-[5,1- a ]isoquinoline derivatives, a kind of valued tricyclic fused 1,2,3-triazoles ( Scheme 1 b). Though some achievements were reached in this field, there is still a lack of strategies for constructing interesting and complex fused 1,2,3-triazole derivatives, which attracts us considerably as we are persistently interested in this area [ 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 ]. Sparked by the vigorous performance of 2-alkynylbenzaldehyde in the synthesis of fused cyclic compounds [ 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 ], herein, we designed 2-(1 H -1,2,3-triazol-5-yl)anilines 1 to react with 2-alkynylbenzaldehydes 2 to construct isoquinolino [2,1- a ] [ 1 , 2 , 3 ] triazolo [1,5- c ] quinazolines 3 through a cascade process involving three C - N bond formations in one manipulation.…”

Section: Introductionmentioning

confidence: 99%

Silver-Catalyzed Cascade Cyclization of Amino-NH-1,2,3-Triazoles with 2-Alkynylbenzaldehydes: An Access to Pentacyclic Fused Triazoles

Zhang

Xiao

et al. 2022

Molecules

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An operationally simple Ag(I)-catalyzed approach for the synthesis of isoquinoline and quinazoline fused 1,2,3-triazoles was developed by a condensation and amination cyclization cascade of amino-NH-1,2,3-triazoles with 2-alkynylbenzaldehydes involving three new C-N bond formations in one manipulation, in which the group of -NH of the triazole ring serves as a nucleophile to form the quinazoline skeleton. The efficient protocol can be applied to a variety of substrates containing a range of functional groups, delivering novel pentacyclic fused 1,2,3-triazoles in good-to-excellent yields.

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“…In this regard, there are several procedures in the literature for the preparation of these N ‐containing polycycles, mainly involving cyclization reactions [12] . Although most of these methods are very effective, and despite the significant recent advances, some limitations are still present, which includes the use of transition metals, such as Fe, [12c] Cu, [12d–f] or Pd, [12g–i] and require various reaction steps and complex starting materials, which are challenging to prepare and environmentally incompatible [12j–l] …”

Section: Introductionmentioning

confidence: 99%

Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines

et al. 2020

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In this work, a one-pot sequential organocatalytic method for the synthesis of fused [1,2,3]triazolo [1,5-a]quinolines through successive cyclization and condensation is presented. In this synthetic strategy, the intermolecular [3 + 2]-cycloaddition occurs between 1,3-dicarbonyl compounds and o-carbonyl-substituted phenylazide compounds, for the formation of the 1,2,3-triazole intermediates. Subsequently, an intramolecular condensation reaction generates the fused quinoline ring by the new CÀ C bond formation, giving the products in yields ranging from moderate to excellent. All the reactions were performed using 20 mol% of 1,8diazabicyclo[5.4.0]undec-7-ene (DBU) as catalyst in the presence of DMSO as solvent at 120°C for 24 h and tolerate a range of 1,3-dicarbonyl compounds, such as β-keto esters and 1,3-diketones, and o-formyl, o-acetyl or o-benzoyl substituted phenylazide compounds.

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Synthesis of Triazole-Fused Phenanthridines through Pd-Catalyzed Intramolecular Phenyl C–H Activation of 1,5-Diaryl-1,2,3-triazoles

Cited by 11 publications

References 6 publications

A Retrosynthetic Approach for Photocatalysis

A Retrosynthetic Approach for Photocatalysis

Silver-Catalyzed Cascade Cyclization of Amino-NH-1,2,3-Triazoles with 2-Alkynylbenzaldehydes: An Access to Pentacyclic Fused Triazoles

Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines

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