<b>The Fischer Reaction of Cyclohexanone Mesitylhydrazone. Evidence of a 1,4-Methyl Migration</b>

Carlin, Robert B.; Moores, Mead S.

doi:10.1021/ja00880a028

Cited by 51 publications

(15 citation statements)

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“…6). The same phenomenon was observed72 when 4,6-dichloro-1,2-benzoquinone-2-diazide (35) reacted with cyclohexanone-2-carboxylic acid to provide 36 in 30% yield (Eq. 7).…”

Section: Preparation Of Arylhydrazines and Hydrazonessupporting

confidence: 69%

Synthesis of the Indole Nucleus

Brown

1971

Chemistry of Heterocyclic Compounds: A Series of Monographs

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“…6). The same phenomenon was observed72 when 4,6-dichloro-1,2-benzoquinone-2-diazide (35) reacted with cyclohexanone-2-carboxylic acid to provide 36 in 30% yield (Eq. 7).…”

Section: Preparation Of Arylhydrazines and Hydrazonessupporting

confidence: 69%

Synthesis of the Indole Nucleus

Brown

1971

Chemistry of Heterocyclic Compounds: A Series of Monographs

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“…In this study, we have synthesized a novel compound N -(2,4dinitrophenyl)-2-fluorobenzohydrazide, C 13 H 9 FN 4 O 5 , characterized by spectroscopic (FT-IR, NMR) and structural (XRD) techniques. Theoretical geometrical parameters by DFT were compared with experimental data results and (17) 121.45 N(4)-C(1)-C (2) 117.22 (16) 117.24 C(7)-C(2)-C (3) 116.71 (16) 116.58 C(7)-C(2)-C (1) 127.07 (17) 126.76 C(3)-C(2)-C (1) 116.22 (16) 116.65 C(4)-C(3)-C (2) 121.19 (17) 121.29 C(5)-C(4)-C(3) 119.81 (18) 120.09 C(6)-C(5)-C(4) 120.37 (18) 119.96 C(7)-C(6)-C (5) 118.63 (18) 118.46 F(1)-C(7)-C (6) 117.32 (17) 116.65 F(1)-C(7)-C (2) 119.41 (17) 119.74 C(6)-C(7)-C (2) 123.26 (18) 123.59 N(1)-C(8)-C (13) 123.14 (17) 122.34 N(1)-C(8)-C (9) 120.72 (17) 120.59 C(13)-C(8)-C (9) 116.14 (17) 117.04 C(10)-C(9)-C (8) 121.85 (18) 121.60 C(9)-C(10)-C (11) 119.48 (18) 119.64 X-ray DFT C(12)-C(11)-C (10) 121.36 (18) 121.03 C(12)-C(11)-N (2) 118.42 (17) 119.42 C(10)-C(11)-N(2) 120.21 (18) 119.54 C(11)-C(12)-C (13) 119.11 (18) 119.43 C(12)-C(13)-C (8) 122.00 (18) 121.20 C(12)-C(13)-N(3) 115.61 (17) 116.50 C(8)-C(13)-N(3) 122.39…”

Section: Resultsmentioning

confidence: 99%

“…In addition, benzohydrazides are also used for the construction of heterocyclic rings due to the presence of carbonyl functionality as well as two nitrogens which can behave like nucleophiles in a number of reactions [8]. Examples of heterocycles include indoles, carbazoles, pyrazoles, triazines, indazolones, and indazoles [9][10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, and DFT Study of N′‐(2,4‐Dinitrophenyl)‐2‐Fluorobenzohydrazide

Saeed

Arshad

Flörke

2013

Journal of Chemistry

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A new hydrazide derivativeN′-(2,4-dinitrophenyl)-2-fluorobenzohydrazide was synthesized and characterized by NMR and IR spectroscopy. The molecular structure was also studied by X-ray diffraction, and the results of the optimized molecular structure are presented and compared with density functional methods with 631-G basis set. The calculated results show that the optimized geometry can well reproduce the crystal structural parameters, for example, bond lengths and angles show good agreement with the experimental data.

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“…N‐Aryl hydrazides form an important class of organic compounds with many applications in organic synthesis and in chemical industry . They are useful starting materials for the synthesis of biologically active heterocycles, such as indazolones, indoles, pyrazoles, carbazoles, triazines, and indazoles …”

Section: Selective C−n Coupling Reactionsmentioning

confidence: 99%

Advances in Selective Carbon‐Heteroatom Coupling Reactions

Zeng

Zhang

Zhou

2018

The Chemical Record

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Most of compounds containing more than one reactive groups may produce several byproducts during the coupling process. Selective carbon-heteroatom coupling reactions, which have merits of high synthetic efficiency and step economy, are the best choice to resolve the problem. Although they have made great progress, they deserve further exploration. This review discusses their recent advances and intend to inspire the research in the future. It is organized on the basis of selective carbon-heteroatom coupling reaction types, including selective C-N and C-N, C-N and C-O, C-O and C-O, C-C and C-N coupling reactions.

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The Fischer Reaction of Cyclohexanone Mesitylhydrazone. Evidence of a 1,4-Methyl Migration

Cited by 51 publications

References 0 publications

Synthesis of the Indole Nucleus

Synthesis of the Indole Nucleus

Synthesis, Crystal Structure, and DFT Study of N′‐(2,4‐Dinitrophenyl)‐2‐Fluorobenzohydrazide

Advances in Selective Carbon‐Heteroatom Coupling Reactions

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