19732-54-8Relevant academic research and scientific papers
Novel SO3H-functionalized ionic liquids - Catalyzed facile and efficient synthesis of polyhydroquinoline derivatives via Hantzsch condensation under ultrasound irradiation
Li, Bai Lin,Zhong, Ai Guo,Ying, An Guo
, p. 445 - 449 (2014)
A facile and efficient synthesis of polyhydroquinolines has been developed via four-component condensation reactions of aldehydes, dimedone, ethyl acetoacetate, and ammonium acetate in the presence of Novel SO3H-functionalized ionic liquid catalysts through Hantzsch reaction under ultrasound irradiation without solvent. Simple work-up procedure, environmentally friendly, inexpensive, and non-toxic catalyst, shorter reaction times along with excellent product yields are the significant features of this practical method.
Methyl 2,7,7-trimethyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3- carboxylate and 3-acetyl-2,7,7-trimethyl-4-phenyl-1,4,5,6,7,8-hexahydro-5-quinolone
Morales, Angel Dago,Garcia-Granda, Santiago,Navarro, Margarita Suarez,Diviu, Alhmed Morales,Perez-Barquero, Remberto Espinosa
, p. 2356 - 2359 (1996)
The 1,4-dihydropyridine (1,4-DHP) ring and the cyclohexanone ring adopt similar conformations in both the title compounds, methyl 2,7,7-trimethyl-4-(3-nitro-phenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3- carboxylate, C20H22N2O5, (I) and 3-acetyl-2,7,7-trimethyl-4-phenyl-1,4,5,6,7,8-hexahydro-5-quinolone, C20H23NO2, (II). The 1,4-DHP rings have boat conformations with the aryl group occupying the pseudo-axial position and orthogonal to the plane through the 1,4-DHP ring. The cyclohexanone ring has an intermediate half-chair/sofa form. In both compounds, the carboxyl group is coplanar to the endocyclic double bond as a consequence of π conjugation. The molecules are linked by N-H...O hydrogen bonds but the packing is different in each case. In compound (I) a hydrogen bond is formed between the N-H and the carboxyl group while in compound (II), a hydrogen bond is formed between the N-H and the O atom of the cyclohexanone ring.
Efficient synthesis of decahydroacridine-1,8-diones and polyhydroquinolines using the step-wise method
Hosseininasab, Fatemeh Sadat,Memarian, Hamid Reza
, p. 1515 - 1540 (2022/01/11)
Various symmetrical and unsymmetrical decahydroacridine-1,8-dione and polyhydroquinoline derivatives were synthesized via two-step cyclocondensation reactions. The advantages of this step-wise addition of reactants in comparison with other one-pot reactions are avoiding the formation of 2 or 3 undesired by-products, therefore allowing cleaner work up of reaction. The important factor of this effective cyclocondensation method is that the prepared β-enaminone component was added dropwise to the solution, in which the Knoevenagel condensation product is slowly being formed by reaction of aldehyde molecule and 1,3-dicarbonyl compounds. The results of the proposed step-wise method are compared and discussed with those obtained in the one-pot reactions.
5-Pyrrolidin-2-yltetrazole-promoted one-pot hantzsch polyhydroquinoline synthesis using NH4HCO3 as nitrogen source
Su, Weike,Li, Jia,Li, Jianjun
experimental part, p. 860 - 863 (2009/04/04)
A straightforward and green synthesis of polyhydroquinoline derivatives was reported via a four-component coupling reaction of aldehydes, dimedone, active methylene compounds, and ammonium bicarbonate in the presence of 5-pyrrolidin-2-yltetrazole under solvent-free conditions. The method offers several advantages including high yields, an environmental friendly procedure, a short reaction time, and easy isolation of products.
COMPETITIVE REACTIONS OF β-DICARBONYL AND β-AMINOVINYLCARBONYL COMPOUNDS WITH ALDEHYDES IN THE SYNTHESIS OF HEXAHYDROQUINOLINES
Dreimane, A. Ya.,Grinshtein, E. E.,Stankevich, E. I.
, p. 612 - 616 (2007/10/02)
It was established that the previously found regularity in the formation of unsymmetrical 5-oxo-2,7,7-trimethyl-4-R'-3-R-1,4,5,6,7,8-hexahydroquinolines or symmetrical 3,3,6,6-tetramethyl-9-R'-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones from β-dicarbonyl and β-aminovinylcarbonyl compounds and an aldehyde, depending on the conditions, is also valid for acetylacetone and benzoylacetone.The competitive character of β-dicarbonyl and β-aminovinylcarbonyl compounds in the reaction was established.The order of formation of the hexahydroquinolines was determined.
