Indole-3-Acetic Acids and Hetero Analogues by One Pot Synthesis including Heck Cyclisation

Wensbo, David; Annby, Ulf; Gronowitz, Salo

doi:10.1016/0040-4020(95)00601-4

Cited by 61 publications

(22 citation statements)

References 41 publications

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“…The cyclization of o-halo N-allylaniline has been applied to the preparation of cycloprop[c]indol-5-ones, 7 indole-3-acetic acids and hetero analogs, 13 indole-3-pyruvic acid oxime ether, 14 5-(sulfamoylmethyl)indoles, 15 the anti-migraine agent CP-122,288, 16 and the protected A-unit of CC-1065. 17 In addition, the cyclization of o-vinylaniline has been applied to o-vinyl-N-tosylanilines, 9,18 o-vinylacetanilides, 19 and o-vinyl-Nalkylanilines.…”

Section: E Applicationsmentioning

confidence: 99%

Hegedus Indole Synthesis

2010

Comprehensive Organic Name Reactions and Reagents

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The palladium (II) complex–catalyzed oxidative N ‐heterocyclization of o ‐allylaniline or o ‐aminostyrenes and the palladium‐catalyzed intramolecular cyclization of o ‐halo N ‐allylaniline are included in the indole derivatives reactions which is referred to as the Hegedus indole synthesis also known as the Hegedus cyclization. Several features of this reaction have been discussed. This reaction is not restricted to nitrogen nucleophiles and it works for oxygen nucleophiles as well. For the preparation of an indole from o ‐halo N ‐allylaniline, the iodo aromatics give good yields of indole in the presence of Pd(OAc) 2 and Et 3 N in CH 3 CN at 110°C for 72 h but it is found necessary to add fresh catalyst periodically. Further this reaction has been explored to form 3‐methylindole in higher yields and under milder conditions without using a phosphine ligand. This reaction has been applied in various organic syntheses.

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Section: E Applicationsmentioning

confidence: 99%

Hegedus Indole Synthesis

2010

Comprehensive Organic Name Reactions and Reagents

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“…During the past few decades, transition-metal-catalyzed reactions have offered a powerful tool for the construction of C–C and C–heteroatom bonds. The application of these reactions such as Heck coupling catalyzed by palladium − and C–H functionalization by Rh 2 (OAc) 4 in the synthesis of indole-3-acetic acid derivatives, which greatly enriched the diversity of substrate structures, has also been explored. Despite these advances, the development of a straightforward method to access indole-3-acetic acid through a one-pot process would be of great value.…”

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confidence: 99%

One-Pot Synthesis of Indole-3-acetic Acid Derivatives through the Cascade Tsuji–Trost Reaction and Heck Coupling

Chen

et al. 2018

J. Org. Chem.

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A practical palladium-mediated cascade Tsuji-Trost reaction/Heck coupling of N-Ts o-bromoanilines with 4-acetoxy-2-butenonic acid derivatives using a Pd(OAc)/P( o-tol)/DIPEA system is described for a straightforward synthesis of indole-3-acetic acid derivatives. This methodology was successfully applied to synthesize various substituted indole/azaindole-3-acetic acid derivatives and Almotriptan, which is a drug for the acute treatment of migraines. Moreover, a plausible cyclization mechanism has been proposed.

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“…In our ongoing efforts to synthesize bioisosteres of functionalized indoles such as oxindole, we became interested in the thienopyrrolone ring system. While an extensive literature exists on the synthesis of the related thienopyrroles [10,11], only a few groups discuss the preparation of thienopyrrolones [12][13][14][15][16]. A common feature in many of these reports is the need to employ highly substituted thiophenes as starting materials, many of which are difficult to prepare.…”

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confidence: 99%