Highly regioselective synthesis of fused seven-membered rings through copper-catalyzed cross-coupling

Sang, Peng; Yu, Ming; Tu, Hang-Fei; Zou, Jian‐Wei; Zhang, Yuhong

doi:10.1039/c2cc37891d

Cited by 52 publications

(22 citation statements)

References 32 publications

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“…Based on previous reports 8,25 and on our preliminarily mechanistic experiments, a possible reaction mechanism was proposed (Scheme 4). Under basic conditions, the intermediate A is initially formed through direct nucleophilic substitution of the phenolic oxygen anion with the 4,5-dichloropyridazin-3-one.…”

Section: Letter Syn Lettmentioning

confidence: 96%

“…[18][19][20][21] On the basis of this concept, many N-and O-containing fused heterocycles have been conveniently produced with high efficiencies. 8,[22][23][24] Inspired by the reported works, 9,10,25 we developed a one-pot, highly regioselective protocol for the construction of indole-fused pyridazino [4,5-b] [1,4]benzoxazepin-4(3H)-ones through a Smiles rearrangement, using readily available starting materials.…”

Section: Letter Syn Lettmentioning

confidence: 99%

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One-Pot Highly Regioselective Synthesis of Indole-Fused Pyridazino[4,5-b][1,4]benzoxazepin-4(3H)-ones by a Smiles Rearrangement

Jiang

2018

Synlett

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A simple and convenient synthesis of indole-fused pyridazino[4,5-b][1,4]benzoxazepin-4(3H)-ones is described. A range of 2-(1H-indol-2-yl)phenols and 4,5-dichloropyridazin-3-ones are compatible with this reaction. A Smiles rearrangement is proposed as a key step in the highly regioselective construction of the products. The easy availability of the starting materials makes this an appealing method in organic synthesis.

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Section: Letter Syn Lettmentioning

confidence: 96%

Section: Letter Syn Lettmentioning

confidence: 99%

One-Pot Highly Regioselective Synthesis of Indole-Fused Pyridazino[4,5-b][1,4]benzoxazepin-4(3H)-ones by a Smiles Rearrangement

Jiang

2018

Synlett

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“…Sang et al [8] reported a protocol for the one-pot synthesis of indole/benzimidazole-fused DBOs 9 via copper catalysis (Scheme 2). The reaction involves a copper initiated C-N and C-O coupling of 2-halophenols 7 and 2-(2-halophenyl)-1H-indoles 8 in one pot.…”

Section: Synthetic Strategies To Dbosmentioning

confidence: 99%

Recent advances in dibenzo[b,f][1,4]oxazepine synthesis

Zaware

Ohlmeyer

2014

Heterocyclic Communications

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Dibenzo[b,f] [1,4]oxazepine (DBO) derivatives possess an array of pharmacological activities, and are of growing pharmaceutical interest. Twelve recent synthetic protocols to construct DBO and DBO derivatives have been described in this review. The reported methods include cyclocondensation with two precursors exemplified by substituted 2-aminophenols and substituted 2-halobenzaldehydes, substituted 2-nitro-1-bromobenzene and substituted 2-triazolylphenols, substituted 2-nitro-1-bromobenzene and substituted 2-hydrazonamidophenol, substituted 2-nitro-1-bromobenzene and substituted 2-(aminomethyl)phenol, and 2-aminobenzonitrile and 1,4-dichloro-2-nitrobenzene. Other methods include copper catalysis, 1,3-dipolar cycloaddition, domino elimination-rearrangement-addition sequence, and an Ugi four-component reaction followed by an intramolecular O-arylation. These methods will serve as a guide to chemists in developing DBO derivatives of pharmacological interest.

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“…Ullman coupling/rearrangement/cyclization cascades are not limited to benzamides and Zhang et al. reported a related reaction with 2‐arylindole 31 to afford a pentacyclic ring system 33 as a single regioisomer (Scheme ) . A range of halogenated phenols 32 were used for the rearrangement and a single halogen is sufficient for activation (i.e., I 90 % and Br 58 %).…”

Section: Two‐electron Smiles Rearrangementmentioning

confidence: 99%

Modern Aspects of the Smiles Rearrangement

Holden

Greaney

2017

Chemistry A European J

165

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The Smiles rearrangement is an intramolecular S Ar reaction, breaking a C-X single bond and forming a new C-X or C-C bond though ipso substitution. Its vast scope, in terms of nucleophile, leaving group, and ring-size of the transition state, make it a powerful tool for arene functionalization, as it can be employed strategically to switch easily-forged bonds with more difficult connections that would be challenging to realize in the intermolecular mode. The reaction has received significantly renewed attention in recent years, as advances in areas such as arene C-X bond formation and radical generation have been harnessed for new arene syntheses through Smiles chemistry. In addition, new reaction modes have been discovered, such as the Clayden rearrangement of lithiated ureas, creating innovative applications for Smiles rearrangements in asymmetric arylation. This Minireview will discuss advances in these areas in the recent literature, covering both two-electron, polar Smiles rearrangements along with single-electron radical transformations.

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Highly regioselective synthesis of fused seven-membered rings through copper-catalyzed cross-coupling

Cited by 52 publications

References 32 publications

One-Pot Highly Regioselective Synthesis of Indole-Fused Pyridazino[4,5-b][1,4]benzoxazepin-4(3H)-ones by a Smiles Rearrangement

One-Pot Highly Regioselective Synthesis of Indole-Fused Pyridazino[4,5-b][1,4]benzoxazepin-4(3H)-ones by a Smiles Rearrangement

Recent advances in dibenzo[b,f][1,4]oxazepine synthesis

Modern Aspects of the Smiles Rearrangement

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