Beiträge zur Chemie der Enaminoketone; 12. Mitteilung<sup>1</sup>. Formylierung von heterocyclischen<i>CH</i>-aciden Verbindungen mit Orthocarbonsäure-triestern und Arylaminen

L'Eplattenier, F.; Vuitel, L.; Junék, H.; Wolfbeis, Otto S.

doi:10.1055/s-1976-24117

Cited by 23 publications

(4 citation statements)

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“…Silica gel 60 (particle size 63−200 μm (70−230 mesh ASTM)) from Kanto Chemical Co. Ltd. was used. N -Vinylamides and -imides 1c − f , dimethylphenylsilane, Rh 2 (OAc) 4 , Rh 2 [(CO) 4 Cl] 2 , Rh(acac) 3 , RhH(PPh 3 ) 4 , and [RhCl(C 6 H 10 )] 2 were purchased from Aldrich or Chisso Co. Ltd. Enamides 1b , 1g , 1h ,and 1i 19 and allylic amides 3a , 3b , 3c , and 3d 22 were prepared as reported previously. RhCl(PPh 3 ) 3 was prepared by a published procedure.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Structure ofN-(Silylalkyl)amides: Rhodium-Catalyzed Hydrosilylation of Enamides

et al. 1998

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Rh(II) acetate effectively catalyzed the hydrosilylation of enamides, N-vinylurea, and imides to give N-(silylalkyl)amide derivatives in moderate to high yields. The silyl group was selectively introduced to the carbon atom adjacent to the nitrogen atom, whereas the efficiency and regioselectivity of the Rh-catalyzed hydrosilylation of vinyl carboxylates, thiocarboxylates, ethers, and thioethers were highly affected by the substitution patterns of the substrates and reaction conditions. The reaction of N-vinylphthalimide (1f) with deuteriosilane suggests that the catalytic process involving the oxidative addition of hydrosilane and migratory insertion of the alkenyl group of 1f is reversible. The molecular structures of the N-(1-silylethyl)phthalimide 2f and N-(1-silylethyl)acetamide 2k species have been determined by X-ray analyses. The results show that there is no intramolecular interaction between the silicon atom and the oxygen atom of the carbonyl groups of 2f and 2k.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Structure ofN-(Silylalkyl)amides: Rhodium-Catalyzed Hydrosilylation of Enamides

et al. 1998

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“…Starting from 3-hydroxyphenalenone 3a, 2-phenylaminomethylene-phenalendione 18 was obtained by reaction with aniline and triethyl orthoformate similar to phenylaminomethylene compounds described earlier [21]. Hydrolysis of 18 should give 3-hydroxy-1-oxo-1H-phenalene-2-carbaldehyde, which could serve as intermediate to form phenaleno-isoxazoles.…”

Section: Cyclization Reaction Of 2-acetyl-3-hydroxyphenalenone 21 To ...mentioning

confidence: 99%

“…Hydrolysis of 18 should give 3-hydroxy-1-oxo-1H-phenalene-2-carbaldehyde, which could serve as intermediate to form phenaleno-isoxazoles. However, this well known reaction [21] did not work in the phenalenone series. Attempts to perform a cleavage of the aniline and chlorination in a one-pot synthesis gave a completely other result, and a naphtho [1,8-bc]acridinone was formed by cyclization [8].…”

Section: Cyclization Reaction Of 2-acetyl-3-hydroxyphenalenone 21 To ...mentioning

confidence: 99%

Syntheses and Reactions of Amino- and Azidophenalenones

Stadlbauer

Fischer

Lackner

2014

Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry

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3-Hydroxyphenalenones 3, synthesized from 1,8-naphthalic anhydride 1 and malonates 2, react by electrophilic halogenation to 2-chlorophenalenediones 4 or 2-iodophenalenone 5. The chloro group of 4 was exchanged against azide by reaction with sodium azide to give 2-azidophenalenediones 6. Nucleophilic chlorination of 3 furnishes 3-chlorophenalenones 7, which were converted to 3-azidophenalenones 8. Staudinger reaction of 8 with triphenylphosphane gave phosphazenes 9 which hydrolyzed to 3-aminophenalenones 10. Amines 10 can also be obtained directly from 3-hydroxyphenalenones 3 and ammonium acetate, or by catalytic hydrogenolysis of azides 8. Nitration of 3-hydroxyphenalenone 3a with nitric acid forms 2-nitrophenalenone 11, which was converted to 3-chloro-2-nitrophenalenone 12. Attempts to introduce the 3-azido group in 12, however, resulted in an exchange of both, the nitro group and the chloro group, to form 2,3-diazidophenalenone 13.2-Amino-3-hydroxyphenalenone 14 cyclizes with carboxylic acid derivatives to oxazolo-phenalenones 15, which were also obtained from 3-azidophenalenone 8a and a carboxylic acid involving an azirine intermediate 16. This allows to move the position of the N-atom. Another cyclization reaction leads via the intermediate oxime 22 of 2-acetylphenalenone 21, which gives an isomer mixture of isoxazolophenalenone 23 as main product and oxazolophenalenone 15 as by-product, because of a parallel reaction via a Beckmann rearrangement.cyclization reactions [8][9][10][11]. In this paper we investigate the synthesis of aminophenalenones and azidophenalenones, their reactivity against electrophilic and nucleophilic reactions and their ability for ring closure reactions to phenaleno-oxazoles and isoxazoles. Synthesis of 3-hydroxyphenalenones 3.Electrophilic halogenation to 4 and 5.

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“…Two of these, compounds 127, R = 6-CI or 7-Me, have been hydrolysed to the quinolones 128, R = 6-C1 or 7-Me and another, 127, R = H gave the quinolthione 129, orthoformate, 4-hydroxy-2-quinolone, and aniline condensed in ethylene glycol at 180°C to give the enamine 130, which was hydrolysed with dilute sodium hydroxide to the aldehyde 131a 344. The alkaloid N-methylllindersine 132 was ozonolysed to the aldehyde 131b.…”

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confidence: 99%

Quinoline Aldehydes

Greenhill¹

1990

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Beiträge zur Chemie der Enaminoketone; 12. Mitteilung¹. Formylierung von heterocyclischenCH-aciden Verbindungen mit Orthocarbonsäure-triestern und Arylaminen

Cited by 23 publications

References 0 publications

Synthesis and Structure ofN-(Silylalkyl)amides: Rhodium-Catalyzed Hydrosilylation of Enamides

Synthesis and Structure ofN-(Silylalkyl)amides: Rhodium-Catalyzed Hydrosilylation of Enamides

Syntheses and Reactions of Amino- and Azidophenalenones

Quinoline Aldehydes

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Beiträge zur Chemie der Enaminoketone; 12. Mitteilung1. Formylierung von heterocyclischenCH-aciden Verbindungen mit Orthocarbonsäure-triestern und Arylaminen

Cited by 23 publications

References 0 publications

Synthesis and Structure ofN-(Silylalkyl)amides: Rhodium-Catalyzed Hydrosilylation of Enamides

Synthesis and Structure ofN-(Silylalkyl)amides: Rhodium-Catalyzed Hydrosilylation of Enamides

Syntheses and Reactions of Amino- and Azidophenalenones

Quinoline Aldehydes

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Product

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Beiträge zur Chemie der Enaminoketone; 12. Mitteilung¹. Formylierung von heterocyclischenCH-aciden Verbindungen mit Orthocarbonsäure-triestern und Arylaminen