Acid-catalyzed reactions of cyclobutanones. III. Formation of substituted 2-tetralones from α-phenylcyclobutanones

1978 ◽  
Vol 56 (1) ◽  
pp. 99-103 ◽  
Author(s):  
Victor P. Abegg ◽  
Alan C. Hopkinson ◽  
Edward Lee-Ruff
Keyword(s):  
Room Temperature ◽  
Phosphorous Pentoxide ◽  
Naphthalene Derivatives ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

A series of cyclobutanones 1–5 were found to rearrange to β-tetralones 6–10, respectively, in the presence of phosphorous pentoxide in benzene at room temperature. The structures of the β-tetralones were inferred by conversion of a number of these known naphthalene derivatives. Possible mechanistic pathways are discussed.

Anomalous acid-catalyzed reactions of cyclobutanones

1969 ◽  
Vol 47 (15) ◽  
pp. 2797-2802 ◽  
Author(s):  
Edward Lee-Ruff ◽  
Nicholas J. Turro ◽  
P. Amice ◽  
J. M. Conia
Keyword(s):  
Carboxylic Acids ◽  
Polyphosphoric Acid ◽  
Ring Cleavage ◽  
Phosphorous Pentoxide ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

The reactions of 2(2-isopropanol)cyclobutanones with phosphorous pentoxide lead to ring opened carboxylic acids. Reaction of 2-isopropylidenecyclobutanones with polyphosphoric acid (PPA) gives ring cleavage rearrangement products. The mechanisms of these reactions are discussed in the light of the observed different reactions of the corresponding cyclopentanones.

Lactic acid-catalyzed fusion of ninhydrin and enamines for the solvent-free synthesis of hexahydroindeno[1,2-b]indole-9,10-diones

2016 ◽  
Vol 22 (3) ◽  
Author(s):  
Xuwen Chen ◽  
Yunyun Liu
Keyword(s):  
Lactic Acid ◽  
Room Temperature ◽  
Solvent Free ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
Solvent Free Synthesis

AbstractThe lactic acid-catalyzed reactions of ninhydrin and secondary enaminones were conducted by solvent-free grinding at room temperature to yield polycyclic 4b,9b-dihydroxy-4b,5,6,7,8,9b-hexahydroindeno[1,2-

Naturally Occurring Organic Acid-catalyzed Facile Diastereoselective Synthesis of Biologically Active (E)-3-(arylimino)indolin-2-one Derivatives in Water at Room Temperature

2019 ◽  
Vol 23 (16) ◽  
pp. 1778-1788 ◽  
Author(s):  
Gurpreet Kaur ◽  
Arvind Singh ◽  
Kiran Bala ◽  
Mamta Devi ◽  
Anjana Kumari ◽  
...  
Keyword(s):  
Room Temperature ◽  
Biologically Active ◽  
Environmentally Benign ◽  
Diastereoselective Synthesis ◽  
Substituted Anilines ◽  
Reaction Conditions ◽  
Naturally Occurring ◽  
Acid Catalyzed ◽  
Reaction Media ◽  
Column Chromatographic

A simple, straightforward and efficient method has been developed for the synthesis of (E)-3-(arylimino)indolin-2-one derivatives and (E)-2-((4-methoxyphenyl)imino)- acenaphthylen-1(2H)-one. The synthesis of these biologically-significant scaffolds was achieved from the reactions of various substituted anilines and isatins or acenaphthaquinone, respectively, using commercially available, environmentally benign and naturally occurring organic acids such as mandelic acid or itaconic acid as catalyst in aqueous medium at room temperature. Mild reaction conditions, energy efficiency, good to excellent yields, environmentally benign conditions, easy isolation of products, no need of column chromatographic separation and the reusability of reaction media are some of the significant features of the present protocol.

Photoinduced rearrangement of hydroxymethylisoxazolines, a route to enaminoaldehydes

1986 ◽  
Vol 51 (10) ◽  
pp. 2167-2180 ◽  
Author(s):  
Lubor Fišera ◽  
Nadezhda D. Kozhina ◽  
Peter Oravec ◽  
Hans-Joachim Timpe ◽  
Ladislav Štibrányi ◽  
...  
Keyword(s):  
Thionyl Chloride ◽  
Quantum Yields ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
Photoinduced Rearrangement ◽  
Condensed Heterocycles

3-Aryl-4-R-carbamoyl-5-hydroxymethylisoxazolines (IV) were synthesized by allowing R-NH2 amines with R = H, CH3, C3H7, C6H5C2H5, and NH2 to act on 3-(X-phenyl)-4-oxo-3a,4,6,6a-tetrahydrofuro[3,4-d]isoxazoles (III) with X = H, 4-CH3, 4-OCH3, 2-OCH3, 4-Cl, 2-Cl, 4-F, 2-F, 4-Br, 4-NO2, and 3-NO2. Exposed to radiation, the substances IV give Z-2-hydroxymethylamino-2-aryl-1-formylacrylamides (V) in good yields. The 4-Cl and 4-F substituted Z-derivatives V isomerize irreversibly to the E-derivatives VI if allowed to stand in solvent; the remaining derivatives V are stable. The quantum yields of the photoreaction are from 0.012 to 0.106 in dependence on the substituent X. In all cases where the compounds IV were used for the preparation of condensed heterocycles in conditions of acid-catalyzed reactions, lactones III were preferentially formed; the action of thionyl chloride on IV results in the formation of chloromethyl derivatives VIII, which do not undergo further cyclization.

Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate

2021 ◽  
Author(s):  
Mizzanoor Rahaman ◽  
M. Shahnawaz Ali ◽  
Khorshada Jahan ◽  
Damon Hinz ◽  
Jawad Bin Belayet ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Ethyl Diazoacetate ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

Kinetic modelling of reactions for the synthesis of 2-methyl-5-ethyl pyridine

2021 ◽  
Author(s):  
Emanuele Moioli ◽  
Leo Schmid ◽  
Peter Wasserscheid ◽  
Hannsjoerg Freund
Keyword(s):  
Kinetic Modelling ◽  
Acid Catalyst ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
Kinetics Of

The kinetics of the acid catalyzed reactions of acetaldehyde ammonia trimer (AAT) and paraldehyde (para) to 2-methyl-5-ethyl pyridine (MEP) in the presence of an acid catalyst were investigated systematically. A...

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