Tautomerism in ketomethylquinolines. Part 2. Further results on 2-ketomethylquinolines

Greenhill, John V.; Loghmani-Khouzani, Hossein; Maitland, Derek J.

doi:10.1039/p19910002831

Cited by 24 publications

(23 citation statements)

References 16 publications

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“…1 H NMR spectra of compounds 6-17 (Table 1) show the signals of the vinyl protons at 5.98-6.87 ppm without any signal of methylene protons which are expected to appear at 4-5 ppm [12,13]. The enaminone forms 6b-17b exhibited NH resonances in the range = 15.08-15.93 ppm due to the strong intramolecular hydrogen bonding between the NH proton and the carbonyl oxygen.…”

Section: Resultsmentioning

confidence: 99%

“…IR spectra were taken by a Shimadzu recording spectrometer, Model 435. 1 H NMR and 13 C NMR spectra were recorded on a Bruker 125 MHZ NMR AC80 spectrometer with CDCl 3 as the solvent. Ultraviolet spectra were obtained by a Shimadzu 160 UV spectrometer and mass spectra were taken by a Micromass Platlform II mass spectrometer.…”

Section: Methodsmentioning

confidence: 99%

“…When R is a phenyl group, it has been proven that electron-donating substituents in the para position of the phenyl group reduces the amount of the form 1b but strong electron-withdrawing substituents cause the transformation of form 1a to form 1b due to strong internal hydrogen bonding [9]. Substituents R' in positions 3 and 4 also cause an increase in the ratio of form 1b (6), Et (7), n-Pr (8), i-Pr (9), t-Bu (10), Ph (11), p-Me-C 6 H 4 (12), p-F-C 6 H 4 (13), p-Me 2 N-C 6 H 4 (14), p-(CH 2 ) 4 N-C 6 H 4 (15), p-Cl-C 6 H 4 (16), p-MeO-C 6 H 4 (17).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 6-acylmethylphenanthridine enaminones

Khouzani

Sadeghi²,

Mehrabi

et al. 2005

JICS

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A series of 6-acylmethylphenanthridine derivatives were synthesized by reaction of aliphatic and aromatic esters with 6-methylphenanthridine in the presence of phenyllithium. Enaminone form of the obtained compounds was investigated by spectroscopic methods. The results revealed that the presence of aromatic rings on 3-and 4-position of 2-acylmethylquinolines (6-acylmethylphenanthridines) is the most important factor for the preference of the enaminone form b. It was found that the intramolecular hydrogen bonding is the only factor that can damage aromaticity of the phenanthridine moiety.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of 6-acylmethylphenanthridine enaminones

Khouzani

Sadeghi²,

Mehrabi

et al. 2005

JICS

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“…39) The reaction sequences similar to that delineated in Chart 5 have already been proposed 36,38,39) for these reactions. In conclusion, we have revealed that 1-benzylwye (8) undergoes electrophilic substitution at the 7-position to produce reactive compounds (4 and 12) on treatment with phosgene in the presence of pyridine.…”

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confidence: 93%

“…Although the formation of 18 has already been reported for the reaction of phosgene and triethylamine, 34,35) that of a vinylamine derivative such as 16 from triethylamine has not been reported except for the reactions with perhalogenated acyl chlorides 35) including trichloroacetyl chloride, 36,37) trichloroacetic anhydride, 38) or hexachloroacetone. 39) The reaction sequences similar to that delineated in Chart 5 have already been proposed 36,38,39) for these reactions.…”

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confidence: 99%

Reaction of Phosgene with the Tricycle Related to the Minor Base of Phenylalanine Transfer Ribonucleic Acids.

Itaya

Kanai

2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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1-Benzylwye (8) underwent electrophilic substitution at the 7-position in the presence of phosgene and pyridine in tetrahydrofuran (THF) to afford the 1,4-dihydropyridines (11, 10, and 14) together with the carboxylic acid 6 and its methyl ester 2 after short treatment of the reaction mixture with methanol and then with water. When triethylamine was used instead of pyridine, phosgene reacted with triethylamine rather than 8, producing (E)-3-(diethylamino)propenoyl chloride (17) and diethylcarbamoyl chloride (18).

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ChemInform Abstract: Tautomerism in Ketomethylquinolines. Part 2. Further Results on 2‐ Ketomethylquinolines.

1992

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structure structure (organic substances) K 9000 -043Tautomerism in Ketomethylquinolines. Part 2. Further Results on 2-Ketomethylquinolines.-IR, 1H and 13C NMR investigations reveal that ketomethylquinolines unsubstituted at the α-position of the ketone or bearing nitrile or ester groups at this position occur in solution exclusively as the enaminone tautomers (I) whereas ketomethylquinolines bearing bromine or alkyl groups at the α-carbon occur in solution exclusively as the ketones (II). The preparations of fifteen representatives of types (I) or (II) and of two pyrroloquinolones with "fixed" enaminone structures by conventional, mostly one-step syntheses (acylation, bromination, alkylation) are described in detail. -(GREENHILL, J. V.; LOGHMANI-KHOUZANI, H.; MAITLAND, D. J.; J.

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Tautomerism in ketomethylquinolines. Part 2. Further results on 2-ketomethylquinolines

Cited by 24 publications

References 16 publications

Synthesis of 6-acylmethylphenanthridine enaminones

Synthesis of 6-acylmethylphenanthridine enaminones

Reaction of Phosgene with the Tricycle Related to the Minor Base of Phenylalanine Transfer Ribonucleic Acids.

ChemInform Abstract: Tautomerism in Ketomethylquinolines. Part 2. Further Results on 2‐ Ketomethylquinolines.

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