New approach for the synthesis of 3H-pyrrolo[2,3-c]isoquinoline derivatives

Dixit, Bharat C.; Balog, J.; Riedl, Zsuzsanna; Drahos, László; Hajós, György

doi:10.1016/j.tet.2012.03.011

Cited by 5 publications

(4 citation statements)

References 33 publications

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“…[27] N-aryl substituted 7-azaindoles 10 may be obtained from the reaction of 2-amino-3-alkynyl pyridines with tetrabutylammonium fluoride (Table 1, entry 6). [28] In this cyclization, TBAF acts on the polarization of carbon-carbon triple bond facilitating the nucleophilic nitrogen attack in a 5-endo-dig mode.…”

Section: Transition Metal-free Synthesis Of 7-azaindolesmentioning

confidence: 99%

“…In this case, a mixture of trifluoroacetic acid (TFA) and trifluoroacetic anhydride (TFAA) promoted the cyclization of 2‐amino‐3‐alkynyl pyridines to 2,5‐disubstituted 7‐azaindoles 9 (Table 1, entry 5) [27] . N ‐aryl substituted 7‐azaindoles 10 may be obtained from the reaction of 2‐amino‐3‐alkynyl pyridines with tetrabutylammonium fluoride (Table 1, entry 6) [28] . In this cyclization, TBAF acts on the polarization of carbon‐carbon triple bond facilitating the nucleophilic nitrogen attack in a 5‐ endo ‐dig mode.…”

Section: Synthesis Of 7‐azaindolesmentioning

confidence: 99%

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Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Neto

Zeni

2021

Asian J Org Chem

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This review is intended to highlight the most useful approaches for the synthesis of indole derivatives (azaindoles, carbazoles, carbolines, indazoles, 3H-indoles, indolines, indolizines, isoindoles, and isoindolines), which were described by using transition-metal catalyzed cyclization reactions of alkynes and nitrogen compounds. The methodologies carried out under metal-free conditions will also be illustrated herein. This review will cover the data published mostly in the past decade. Synthesis of 6-AzaindolesAzaindoles, although rare in nature, have attracted a significant attention because some synthetic structures containing this nucleus exhibit biological activities. [17] The synthetic methods describing the preparation of azaindoles are limited. Usually their synthesis was achieved from the cyclization reaction of substrates containing aminopyridines. [18] Transition Metal-Free Synthesis of 6-AzaindolesWe have nominated two methodologies for the preparation of 6-azaindoles, which were developed using alkynes and nitrogen compounds in a metal-free protocol. In the first, an electrophilic cyclization condition, using iodine as an electrophilic source, was applied to 2-(azidomethyl)-3-alkynyl-pyrroles in the preparation of 4-iodo-6-azaindoles 1 (Scheme 1, eq 1). [19] The second approach described the preparation of 2,5-disubstituted 6azaindoles 2 from base-catalyzed intramolecular cyclization of 2-(azidomethyl)-3-alkynyl-pyrroles (Scheme 1, eq 2). [20] 3. Synthesis of 7-Azaindoles Transition Metal-Catalyzed Synthesis of 7-Azaindoles Silver-Catalyzed Synthesis of 7-AzaindolesSilver-catalyzed cyclization reactions of alkynes constitute powerful strategies for the construction of heterocycles. In particular, the 7-azaindoles could be obtained by these approaches. A general method for the preparation of aryl-[a] Dr. J.

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Section: Transition Metal-free Synthesis Of 7-azaindolesmentioning

confidence: 99%

Section: Synthesis Of 7‐azaindolesmentioning

confidence: 99%

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Neto

Zeni

2021

Asian J Org Chem

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“…15 Likewise, Hajós developed a TBAF-promoted 5-endo-dig cyclization involving 4-ethynylisoquinoline-3-amines 3 as a viable route to derivative 2b (Scheme 1a). 16 A few years ago, we reported the synthesis of the pyrrolo[2,3- c ]isoquinoline 8a as a single example of cycloaddition between the ( E )-arylideneaminopyrrole 6e with the aryne derived from 7 (Scheme 1b,i). 17 More recently, we reported an efficient synthesis and significant structural studies by X-ray of a series of ( E )-arylideneaminopyrroles 6a–c and their reduction products to secondary amines 9a–c via a two-step synthesis sequence (solvent-free condensation and reduction) starting from 5-amino-1- tert -butyl-1 H -pyrrole-3-carbonitrile ( 4 ) and arylaldehydes 5 (Scheme 1b,ii).…”

Section: Introductionmentioning

confidence: 99%

“…Specifically, pyrrolo[2,3- c ]isoquinolines synthesis is quite rare, but Biehl et al reported the synthesis of derivative 2a by an acid-promoted cyclization of 4-formylmethylisoquinolin-3-amines 1 . Likewise, Hajós developed a TBAF-promoted 5-endo-dig cyclization involving 4-ethynylisoquinoline-3-amines 3 as a viable route to derivative 2b (Scheme a) . A few years ago, we reported the synthesis of the pyrrolo[2,3- c ]isoquinoline 8a as a single example of cycloaddition between the ( E )-arylideneaminopyrrole 6e with the aryne derived from 7 (Scheme b,i) .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pyrrolo[2,3-c]isoquinolines via the Cycloaddition of Benzyne with Arylideneaminopyrroles: Photophysical and Crystallographic Study

et al. 2019

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An efficient and quick access toward a series of (E)-2-arylideneaminopyrroles 6 and to their benzyne-promoted aza-Diels–Alder cycloaddition products is provided. These products are three pyrrolo[2,3-c]isoquinolines 8a–c substituted in position 5 with different electron-acceptor (A) or electron-donor (D) aryl groups. Intermediates and products were obtained in good yields (up to 78 and 84%, respectively), and their structures were determined on the basis of NMR measurements and HRMS analysis. Photophysical properties of 8a–c were investigated, finding good Stokes shift in different solvents, but only the product 8c showed appreciable fluorescence intensity since its 5-aryl group (2,4-Cl2Ph) could favor the twisted intramolecular charge transfer effect. In addition, a riveting relationship between solvent viscosity and fluorescence intensity was found. Structures of 6 and 8 were studied and confirmed by single-crystal X-ray diffraction, observing that their electronic distributions effect the supramolecular assembly but with only long-distance hydrophobic interactions. A CE-B3LYP model was used to study the energetic topology and understand the crystal architecture of compounds as well as find a connection with both the synthetic and photophysical results.

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Palladium‐Catalyzed Indole Ring Synthesis

2016

Indole Ring Synthesis

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New approach for the synthesis of 3H-pyrrolo[2,3-c]isoquinoline derivatives

Cited by 5 publications

References 33 publications

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Synthesis of Pyrrolo[2,3-c]isoquinolines via the Cycloaddition of Benzyne with Arylideneaminopyrroles: Photophysical and Crystallographic Study

Palladium‐Catalyzed Indole Ring Synthesis

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