In recent years, much attention has been directed towards the syntheses of 1,4-dihydropyridyl compounds due to the fact that 1,4-dihydropyridyl compounds possess a variety of biological activities.[1] In view of the importance of polyhydroquinoline derivatives, many classical methods for the synthesis of polyhydroquinoline derivatives were reported[2] by conventional heating and refluxing approaches in the presence of organic solvent. These methods, however, involve long reaction time, harsh reaction conditions, the use of a large quantity of organic solvent and unsatisfactory yields. Therefore,improvements in such syntheses have been sought continuously.……
In recent years, a wide variety of organic compounds bearing indole fragment have been attracted much attention due to the fact that many of them are pharmacologically and biologically active compounds.[1] Among them β-indolylketones are one of the most significant intermediates for the preparation of natural products such as hapalindole D 1.[2] In recent years, the utilization of multicomponent condensations (MCCs) to generate novel, drug-like scaffolds are replete in current organic reactions due to the fact that products can be prepared directly in a single step and the diversity can be achieved simply by varying the reaction substrates. In continuation of our work to synthesize new β-indolylketones,[3] herein, we report a novel base-induced syntheses of new β-indolylketones via a three-component condensation. Deoxybenzoin as carbonyl compound is introduced into the reaction (Scheme 1), and all the reactions were operated under ultrasound irradiation since the utilization of which can accelerate the progress of many reactions and shorten the reaction time.……
The title compound (C23H22N2O) 3 has been synthesized by the reaction of (S)- (-)-1,1-diphenyl-2-pyrrolidinemethanol 1 with 2-pyridinecarboxaldehyde 2 in refluxing benzene catalyzed by TsOH, and its structure was determined by single-crystal X-ray diffraction. The crystal belongs to orthorhombic, space group P212121 with a = 8.4747(8), b = 10.8829(10), c = 19.777(2) , Mr = 342.43, V =1824.0(3) 3, Dc = 1.247 g/cm3, Z = 4, m = 0.077 mm-1 and F(000) = 728. The structure was solved by direct methods and refined by full-matrix least-squares techniques to the final R = 0.0497 and wR = 0.0927.
LU JunJI Shun-JunQIAN RongJIANG Zhao-QinZHANG YongLANG Jian-Ping
＜正＞As an important class of pharmacologically active compounds, benzodiazepines are widely used in the last de...
GU, Da-Gong WANG, Hong-Xia JI, Shun-Jun Key Lab. of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering of Suzhou University, Suzhou 215006
＜正＞ The importance of the indole nucleus has been well established in pharmaceutical chemistry, as many of its...
WANG, Shun-Yi ZHOU, Wei-Juan XIAO, Feng JI Shun-Jun
(Key Lab. of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering of Suzhou
University, Suzhou 215006)
The investigation of the chemistry of indoles has been, and continues to be, one of the most active areas of heterocyclic chemistry.[1] In particular, β-indolylketones have received much attention as important building blocks for the synthesis of many natural products and other biologically active compounds.[2] In continuation of our work in the synthesis of indole derivates,[3] we describe the remarkable catalytic of PTSA as a cheaper catalyst in ultrasound-accelerated Michael reaction of indole with α, β-unsaturated ketones (2), which provide one of the most efficient routes to the synthesis of β-indolyketones. In all cases, the substitution on the indole nucleus occurred exclusively at the 3-position, and N-alkylation products have not been observed. In addition, the structure of 3a was further confirmed by single crystal X-ray crystallography.……
Indole fragment is featured widely in a wide variety of pharmacologically and biologically active compounds.[1] The 3,3-bis(3-indolyl)oxindole has been shown to possess antibiotic activities against Escherichia coli, Bacillus subtilis and Staphylococcus aureus. [2] As a continue of our work on the synthesis of indole derivates such as bis(indolyl)methanes,[3]we describe an ultrasound-accelerated reaction of isatin 1 with indoles 2 using a catalytic amount of ceric ammonium nitrate (CAN), which provides an efficient route to the synthesis of 3,3-di(1H-indol-3-yl)indolin-2-ones.……
