Studies on the Doebner-Miller, Skraup, and Related Reactions. II. Preparation and Cyclization of 4-(2'-Nitroanilino)-3-methylbutan-2-one

1963 ◽  
Vol 16 (5) ◽  
pp. 828 ◽  
Author(s):  
GM Badger ◽  
BC Ennis ◽  
WE Matthews
Keyword(s):  
Methyl Ethyl Ketone ◽  
Mannich Reaction ◽  
Lewis Acids ◽  
Mannich Base ◽  
Methyl Ethyl ◽  
The Mannich Reaction

The intermediate adduct (e.g. III) formed in Skraup and Doebner-Miller reactions has the nature of a Mannich base. It has now been prepared from o-nitroaniline, formaldehyde, and methyl ethyl ketone by the Mannich reaction. It has been cyclized to 3,4-dimethyl-8-nitroquinoline under acidic oxidizing conditions; but it is not cyclized by neutral oxidants, nor by non-oxidizing acids or Lewis acids.

Synthesis of some new hydrazide-hydrazones related to isatin and its Mannich and Schiff bases

2016 ◽  
Vol 71 (11) ◽  
pp. 1147-1157 ◽  
Author(s):  
Elsayed M. Afsah ◽  
Saad S. Elmorsy ◽  
Soha M. Abdelmageed ◽  
Zaki E. Zaki
Keyword(s):  
Schiff Base ◽  
Schiff Bases ◽  
Mannich Reaction ◽  
Mannich Base ◽  
The Mannich Reaction

AbstractThe hydrazide-hydrazones 6a–d and 7a, b were obtained by treating isatin (1) or its Mannich base 2 with hydrazides incorporating piperidine, morpholine, and piperazine units. The reaction of 1 and 2 with hydrazides related to triazenes having piperidine, morpholine, and 1,2,3,4-tetrahydroisoquinoline moieties gave 12a–c and 13a–c. Treatment of 1 and 2 with iminodiacetohydrazide (14) and ethylenediamine tetraacetohydrazide (18) afforded 15–17 and 19a, b, respectively. The Mannich reaction of the Schiff base 20 with formaldehyde and the appropriate hydrazide or bis(hydrazide) gave 21a, b and 22a, b. The hydrazides related to Schiff bases 20 and 26 were used as precursors in synthesis of compounds incorporating two 2-oxoindoline units or formazan moiety.

scholarly journals Two-Step Synthetic Approach to 6-Substituted Pyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones from 6-Amino-, 6-Alkylamino-, and 6-Arylamino-1,3-dimethyluracils

2006 ◽  
Vol 61 (4) ◽  
pp. 486-494 ◽  
Author(s):  
Kerstin Bischoff ◽  
Ulrich Girreser ◽  
Dieter Heber ◽  
Martin Schütt
Keyword(s):  
Mannich Reaction ◽  
Mannich Base ◽  
Mannich Bases ◽  
Ring Closure ◽  
Synthetic Approach ◽  
Reaction Conditions ◽  
Iminium Salts ◽  
Vilsmeier Formylation ◽  
The Mannich Reaction

The Mannich reaction of 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidines 3, easily accessible by condensation of 6-amino-1,3-dimethyluracil (1) with Mannich bases 2a - c, gives rise to a mixture of 7-aryl-6-(N,N-dimethylaminomethyl)pyrido[2,3-d]pyrimidines 6 and 7 as well as 1,2-bis- (7-arylpyrido[2,3-d]pyrimidin-6-yl)ethane 13 the ratio of which depends on the reaction conditions and the amine used. 6-Alkylamino-1,3-dimethyluracils 15 - 18 were converted to the corresponding 5-(3-oxo-3-phenylpropyl)uracils 19 - 22 by condensation with the Mannich base 2a. Ring closure of 19 - 22 was performed by Vilsmeier formylation to afford the 8-alkyl- and 7,8-diaryl-5,8- dihydropyrido[2,3-d]pyrimidine-6-carbaldehydes 9 - 12 via the corresponding iminium salts 27 - 30

Plant growth regulators in Eucalyptus grandis. V. Synthesis of the G-regulators

1982 ◽  
Vol 35 (7) ◽  
pp. 1421 ◽  
Author(s):  
ML Bolte ◽  
WD Crow ◽  
S Yoshida
Keyword(s):  
Hydrogen Bonding ◽  
Plant Growth ◽  
Growth Regulators ◽  
Mannich Reaction ◽  
Mannich Base ◽  
Eucalyptus Grandis ◽  
High Yield ◽  
Aqueous Acid ◽  
The Mannich Reaction ◽  
Synthetic Approaches

Problems associated with earlier synthetic approaches to the G-regulators have been overcome by the use of the Mannich reaction in aprotic media. Under these conditions the Mannich base formed from the reaction of 1,3-diketones and aldehydes is stabilized by internal hydrogen bonding and can be isolated in high yield. In aqueous acid rapid elimination occurs to give the 2-methylene 1,3-diketones, which first enolize then add oxygen to generate the G-regulator structure. The steric limitations of the reactions are examined.

Highly efficient synthesis of methyl ethyl ketone oxime through ammoximation over Ti-MOR catalyst

2014 ◽  
Vol 34 (1) ◽  
pp. 243-250
Author(s):  
Jianghong DING ◽  
Le XU ◽  
Hao XU ◽  
Haihong WU ◽  
Yueming LIU ◽  
...  
Keyword(s):  
Methyl Ethyl Ketone ◽  
Methyl Ethyl ◽  
Efficient Synthesis ◽  
Highly Efficient

Electroinduced oxidative copolymerization ofN-vinyl carbazole with methyl ethyl ketone formaldehyde resin

2004 ◽  
Vol 15 (7) ◽  
pp. 365-369 ◽  
Author(s):  
Belkıs Ustamehmetoğlu ◽  
A. Sezai Saraç ◽  
Nilgün Kızılcan ◽  
Ahmet Akar
Keyword(s):  
Methyl Ethyl Ketone ◽  
Formaldehyde Resin ◽  
Methyl Ethyl ◽  
Oxidative Copolymerization

scholarly journals Recent advances and prospects in the Zn-catalysed Mannich reaction

RSC Advances ◽  
2021 ◽  
Vol 11 (16) ◽  
pp. 9098-9111
Author(s):  
Salahudeen Shamna ◽  
C. M. A. Afsina ◽  
Rose Mary Philip ◽  
Gopinathan Anilkumar
Keyword(s):  
Carbonyl Compound ◽  
Secondary Amine ◽  
Mannich Reaction ◽  
Mannich Base ◽  
Mannich Reactions ◽  
Recent Advances ◽  
Primary Secondary Amine

Amino alkylation of an acidic α-proton of a carbonyl by formaldehyde and a primary/secondary amine or ammonia, affording a β-amino-carbonyl compound also known as a Mannich base is a valuable reaction. We focus on recent advances in Zn catalysed Mannich reactions.

scholarly journals Lipozyme 435-Mediated Synthesis of Xylose Oleate in Methyl Ethyl Ketone

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3317
Author(s):  
Maria Carolina Pereira Gonçalves ◽  
Jéssica Cristina Amaral ◽  
Roberto Fernandez-Lafuente ◽  
Ruy de Sousa Junior ◽  
Paulo Waldir Tardioli
Keyword(s):  
Oleic Acid ◽  
Methyl Ethyl Ketone ◽  
Molar Ratio ◽  
Methyl Ethyl ◽  
Sugar Ester ◽  
Molar Ratios ◽  
Emulsion Capacity ◽  
Ping Pong ◽  
Commercial Sugar ◽  
Repeated Use

In this paper, we have performed the Lipozyme 435-catalyzed synthesis of xylose oleate in methyl ethyl ketone (MEK) from xylose and oleic acid. The effects of substrates’ molar ratios, reaction temperature, reaction time on esterification rates, and Lipozyme 435 reuse were studied. Results showed that an excess of oleic acid (xylose: oleic acid molar ratio of 1:5) significantly favored the reaction, yielding 98% of xylose conversion and 31% oleic acid conversion after 24 h-reaction (mainly to xylose mono- and dioleate, as confirmed by mass spectrometry). The highest Lipozyme 435 activities occurred between 55 and 70 °C. The predicted Ping Pong Bi Bi kinetic model fitted very well to the experimental data and there was no evidence of inhibitions in the range assessed. The reaction product was purified and presented an emulsion capacity close to that of a commercial sugar ester detergent. Finally, the repeated use of Lipozyme 435 showed a reduction in the reaction yields (by 48 and 19% in the xylose and oleic acid conversions, respectively), after ten 12 h-cycles.

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