POTENTIAL NITROGEN-HETEROCYCLE CARCINOGENS. IV. SYNTHESIS OF 2,3-BENZOCARBAZOLES AND OF INDENOINDOLES<sup>1</sup>

Buu‐Hoï, Ng. Ph.; Hoán, Ng.; Khôi, Ng. H.

doi:10.1021/jo01147a021

Cited by 11 publications

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“…Benzannelated analogs 478 and 479 (Scheme 62) were synthesized from 1-indanone and α-and βnaphthylhydrazones, correspondingly. [214] Since the reaction of N-unsubstituted 5,10-dihydroindeno [1,2-b]indoles with one equivalent of strong base deprotonates the nitrogen atom, N-unsubstituted compounds are not applicable for metallocene synthesis. On the other hand, the desired η 5 -ligand precursors can be readily accessed through deprotonation followed by N-alkylation (Scheme 63A).…”

Section: (3)h-benzo[b]cyclopenta[d]thiophene Derivativesmentioning

confidence: 99%

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Synthesis of Heteroarene‐Fused Cyclopentadienes and Related Compounds Suitable for Metallocene Preparation

Nifant’ev

Ivchenko

2020

Adv Synth Catal

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Metallocene catalysis is widely used in transformations of unsaturated organic compounds, including the bulk industrial synthesis of polyolefins. Over the last few decades, the electronic and structural properties of their η5‐coordinated ligands have been modified by introducing electron‐donating, electron‐withdrawing, and sterically hindered substituents to obtain desirable catalytic properties for the metallocenes. An efficient way to design η5‐coordinated ligands is to exploit the annelation of heterocyclic fragments with a cyclopentadiene ring. In the present review, we summarize, systematize, and analyze synthetic approaches to heterocycle‐fused cyclopentadienes suitable for metallocene catalyst preparation.

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Section: (3)h-benzo[b]cyclopenta[d]thiophene Derivativesmentioning

confidence: 99%

“…Benzannelated dihydroindeno [1,2-b]indoles. [214] Scheme 63. Synthesis of N-substituted dihydroindeno [1,2-b] indoles.…”

Section: Indeno[12-b]indole and Related Compoundsmentioning

confidence: 99%

Synthesis of Heteroarene‐Fused Cyclopentadienes and Related Compounds Suitable for Metallocene Preparation

Nifant’ev

Ivchenko

2020

Adv Synth Catal

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Bucherer Carbazole Synthesis

2010

Comprehensive Organic Name Reactions and Reagents

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The synthesis of carbazoles from aryl hydrazines, sodium bisulfite, and 1‐ or 2‐naphthols (or 1‐ or 2‐naphthylamines) and is generally referred to as the Bucherer carbazole synthesis or Bucherer reaction. The study finds that sulfonation of naphthylamine might be the early step in the reaction pathway. This reaction so far has been the most commonly used preparation of dibenzocarboles. This reaction has been modified by using aryl hydrazine and tetralone in the presence of HCl to form carbazole.

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Six‐Membered Carbocycles

2010

Name Reactions for Carbocyclic Ring Formations

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POTENTIAL NITROGEN-HETEROCYCLE CARCINOGENS. IV. SYNTHESIS OF 2,3-BENZOCARBAZOLES AND OF INDENOINDOLES¹

Cited by 11 publications

References 0 publications

Synthesis of Heteroarene‐Fused Cyclopentadienes and Related Compounds Suitable for Metallocene Preparation

Synthesis of Heteroarene‐Fused Cyclopentadienes and Related Compounds Suitable for Metallocene Preparation

Bucherer Carbazole Synthesis

Six‐Membered Carbocycles

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POTENTIAL NITROGEN-HETEROCYCLE CARCINOGENS. IV. SYNTHESIS OF 2,3-BENZOCARBAZOLES AND OF INDENOINDOLES1

Cited by 11 publications

References 0 publications

Synthesis of Heteroarene‐Fused Cyclopentadienes and Related Compounds Suitable for Metallocene Preparation

Synthesis of Heteroarene‐Fused Cyclopentadienes and Related Compounds Suitable for Metallocene Preparation

Bucherer Carbazole Synthesis

Six‐Membered Carbocycles

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POTENTIAL NITROGEN-HETEROCYCLE CARCINOGENS. IV. SYNTHESIS OF 2,3-BENZOCARBAZOLES AND OF INDENOINDOLES¹