Indoles

Грандберг, И. И.; Belyaeva, L. D.; Dmitriev, L. B.

doi:10.1007/bf00510019

Cited by 6 publications

(6 citation statements)

References 5 publications

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“…“Direct arylation”1 has emerged over the past few years as an outstanding alternative to traditional cross‐coupling reactions2 in the preparation of biaryl molecules because this strategy partially avoids the need of stoichiometric organometallic activating groups. Since the indole nucleus is ubiquitous in materials science, pharmaceutical and natural products,3 major improvements have been achieved in the direct and site‐selective arylation of (NH)‐indoles through either Pd‐, Rh‐ or Cu‐catalyzed methodologies 4. Nevertheless, to the best of our knowledge no report focuses on complementary C2‐5 and C3‐arylation6 procedures by means of a unique catalytic system 7.…”

Section: Methodsmentioning

confidence: 99%

“On Water” Direct and Site‐Selective Pd‐Catalysed CH Arylation of (NH)‐Indoles

Joucla¹,

Batail²,

Djakovitch³

2010

Adv Synth Catal

149

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This communication describes the development of a versatile catalytic system based on palladium(II) acetate/bis(diphenylphosphino)methane [PdA C H T U N G T R E N N U N G (OAc) 2 /dppm] that works "on water" giving site-selective C À H arylation of (NH)-indoles without protecting or directing groups. Remarkably, the control of regioselectivity was achieved by small changes in the "extra-catalytic" base/halide partners. These innovative methodologies allow a highyielding access to both C2 and C3-arylindoles, as well as 2,3-diarylindoles, and display high chemo/regioselectivities and structural versatility with regard to either indole or aryl moieties.

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Section: Methodsmentioning

confidence: 99%

“On Water” Direct and Site‐Selective Pd‐Catalysed CH Arylation of (NH)‐Indoles

Joucla¹,

Batail²,

Djakovitch³

2010

Adv Synth Catal

149

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“…For related literature on indole derivatives, see: Farhanullah et al (2004); Noland & Hammer (1960); Sundberg (1996); Wu et al (1972).…”

Section: Related Literaturementioning

confidence: 99%

“…Indole has potentially reactive sites for a variety of chemical reactions to generate molecular diversity (Farhanullah et al, 2004). Indole derivatives, either natural or synthetic products, have been widely studied because of their therapeutic importance (Sundberg, 1996). Indoles are known to dimerize and trimerize in acidic media (Noland et al, 1960), and the derivatives of the indole dimer, i.e.…”

Section: S1 Commentmentioning

confidence: 99%

1-Methyl-3-(1-methyl-2,3-dihydro-1H-indol-2-yl)-1H-indole

2007

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CommentIndole has potentially reactive sites for a variety of chemical reactions to generate molecular diversity (Farhanullah et al., 2004). Indole derivatives, either natural or synthetic products, have been widely studied because of their therapeutic importance (Sundberg, 1996). Indoles are known to dimerize and trimerize in acidic media (Noland et al., 1960), and the derivatives of the indole dimer, i.e. a series of 1-imidoyl-2-(2-and 3-indolyl)indolines, are found to present potential diuretic activity (Wu et al., 1972). The title compound (I) was synthesized by dimerization of N-methylindole in the presence of iodine as a catalyst. Herein we report the crystal structure of (I).The molecular structure of (I) is shown in Fig.1. A l l bond distances and angles are normal. The length of the bond linking the indole and the indoline rings (C2-C10) is 1.486 (3) Å. The indoline ring adopts an envelope conformation with atom C10 deviating from the N2/C11/C12/C17 plane by 0.501 (3) Å. The indole ring and the indoline ring are approximately perpendicular, and the dihedral angle between them is 86.30 (3)°. ExperimentalA mixture of N-methylindole (10 mmol) and I 2 (1 mmol) was stirred in acetonitrile (30 ml) at room temperature for a few s.After completion of the reaction (TLC, < 1 min), the mixture was treated with aqueous Na 2 S 2 O 3 solution (5%, 30 ml). The product was extracted with ethyl acetate (3 × 30 ml). The combined organic layer was dried with anhydrous sodium sulfate, and purified by column chromatography (ethyl acetate:petroleum ether = 1:20) to afford the title compound (85% yield).Recrystallization by slow evaporation of a methanol solution was carried out to obtain good, diffraction quality crystals. RefinementAll H atoms were positioned geometrically and allowed to ride on their respective parent atoms, with C-H = 0.93, 0.96, 0.97 or 0.98 Å and U iso (H) = 1.2 or 1.5 U eq (C).

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“…The indole ring system is present in numerous natural products, pharmaceuticals, agrochemicals and other compounds of importance . Particularly, N ‐arylated indole motifs are very important as they exhibit nanomolar affinity for α 1 ‐adrenoceptors in addition to their affinities for dopamine D 2 and serotonin 5‐HT 2A receptors .…”

Section: Introductionmentioning

confidence: 99%

“…Of the many methods for the synthesis of N ‐arylindoles, the Fisher indole synthesis is the best known and most widely used . Ullmann‐type coupling methodology, involving the combination of an indole with an aryl halide in the presence of base and a copper catalyst at high temperatures, is an important alternative .…”

Section: Introductionmentioning

confidence: 99%

SBA‐15‐functionalized melamine–pyridine group‐supported palladium(0) as an efficient heterogeneous and recyclable nanocatalyst for N‐arylation of indoles through Ullmann‐type coupling reactions

Veisi

Heravi

Hamelian

2015

Applied Organom Chemis

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SBA-15-functionalized melamine-pyridine group-supported palladium(0) was found to serve as a heterogeneous and recyclable nanocatalyst for N-arylation of indoles with aryl iodides under a low catalyst loading (0.3 mol% of Pd) through Ullmann-type C-N coupling reactions. A variety of aryl iodides could be aminated to provide the N-arylated products in good to excellent yields without the need of an inert atmosphere. Also, this catalyst was found to be an efficient system for the N-arylation of other nitrogen-containing heterocycles with aryl iodides. The heterogeneous palladium catalyst could be recovered by simple filtration of the reaction solution and reused for six cycles without significant loss in its activity.

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Indoles

Cited by 6 publications

References 5 publications

“On Water” Direct and Site‐Selective Pd‐Catalysed CH Arylation of (NH)‐Indoles

“On Water” Direct and Site‐Selective Pd‐Catalysed CH Arylation of (NH)‐Indoles

1-Methyl-3-(1-methyl-2,3-dihydro-1H-indol-2-yl)-1H-indole

SBA‐15‐functionalized melamine–pyridine group‐supported palladium(0) as an efficient heterogeneous and recyclable nanocatalyst for N‐arylation of indoles through Ullmann‐type coupling reactions

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