Efficient synthesis of decahydroacridine-1,8-diones and polyhydroquinolines using the step-wise method

被引：1

作者：

Hosseininasab, Fatemeh Sadat ^{[1
]}

Memarian, Hamid Reza ^{[1
]}

机构：

[1] Univ Isfahan, Dept Chem, Esfahan 8174673441, Iran

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2022年 / 48卷 / 04期

关键词：

Cyclocondensation reaction; Decahydroacridine-1,8-diones; beta-Enaminone; Multi-component reaction; Polyhydroquinolines; ONE-POT SYNTHESIS; SOLVENT-FREE; IONIC LIQUID; 1,4-DIHYDROPYRIDINE DERIVATIVES; MULTICOMPONENT REACTIONS; 4-COMPONENT SYNTHESIS; CATALYST; GREEN; ALDEHYDES; WATER;

D O I：

10.1007/s11164-021-04643-z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 beta-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.

引用

页码：1515 / 1540

页数：26

共 50 条

[41] Measurement and Uncertainty Assessment of the Thermal Conductivity and Diffusivity of Silica Glass using Step-Wise Transient Method
Svetozár Malinarič
Ahmed Elkholy
International Journal of Thermophysics, 2021, 42
[42] Fishing for drifts: detecting buoyancy changes of a top marine predator using a step-wise filtering method
Gordine, Samantha Alex
Fedak, Michael
Boehme, Lars
JOURNAL OF EXPERIMENTAL BIOLOGY, 2015, 218 (23): : 3816 - 3824
[43] Measurement and Uncertainty Assessment of the Thermal Conductivity and Diffusivity of Silica Glass using Step-Wise Transient Method
Malinaric, Svetozar
Elkholy, Ahmed
INTERNATIONAL JOURNAL OF THERMOPHYSICS, 2021, 42 (03)
[44] The step-wise dissolution method: An efficient DSC-based protocol for verification of predicted API-polymer compatibility
Mathers, Alex
Pechar, Matous
Hassouna, Fatima
Fulem, Michal
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2023, 648
[45] Carbon-based nanocatalyst: An efficient and recyclable heterogeneous catalyst for one-pot synthesis of gem-bisamides, hexahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes
Jaspreet Kour
Monika Gupta
Bushra Chowhan
Vivek K. Gupta
Journal of the Iranian Chemical Society, 2019, 16 : 2587 - 2612
[46] Carbon-based nanocatalyst: An efficient and recyclable heterogeneous catalyst for one-pot synthesis of gem-bisamides, hexahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes
Kour, Jaspreet
Gupta, Monika
Chowhan, Bushra
Gupta, Vivek K.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (12) : 2587 - 2612
[47] A convenient synthesis of 9-aryl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones under microwave irradiation without solvent
Tu, SJ
Lu, ZS
Shi, DQ
Yao, CS
Gao, Y
Guo, C
SYNTHETIC COMMUNICATIONS, 2002, 32 (14) : 2181 - 2185
[48] Green and efficient synthesis of acridine-1,8-diones and hexahydroquinolines via a KH2PO4 catalyzed Hantzsch-type reaction in aqueous ethanol
Yu, Shi-Jun
Wu, Si
Zhao, Xin-Min
Lu, Cheng-Wei
RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (05) : 3121 - 3130
[49] Green and efficient synthesis of acridine-1,8-diones and hexahydroquinolines via a KH2PO4 catalyzed Hantzsch-type reaction in aqueous ethanol
Shi-Jun Yü
Si Wu
Xin-Min Zhao
Cheng-Wei Lü
Research on Chemical Intermediates, 2017, 43 : 3121 - 3130
[50] A step-wise numerical thermal control method for advanced composite curing process using digital image based programming
Li, Yingguang
Xu, Ke
Wang, Shixin
Gao, James
Maropoulos, Paul
CIRP ANNALS-MANUFACTURING TECHNOLOGY, 2023, 72 (01) : 441 - 444

← 1 2 3 4 5 →