24243-43-4Relevant academic research and scientific papers
A convenient synthesis of β-carbolines by iron-catalyzed aerobic decarboxylative/dehydrogenative aromatization of tetrahydro-β-carbolines under air
Mohamad Arshad, Ahmad Saifuddin,Meesala, Ramu,Hanapi, Nur Aziah,Mordi, Mohd Nizam
, (2021/02/12)
A convenient synthesis for the conversion of various substituted tetrahydro-β-carbolines has been developed by iron-catalyzed decarboxylative/dehydrogenative aromatization to construct aromatic β-carbolines under air atmosphere. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce corresponding β-carbolines in good yields in the absence of any additive. Additionally, the utility of the method was highlighted in the gram-scale synthesis of important natural β-carboline synthons norharmane (2a) and harmane (2b), which the latter provide practical access towards eudistomin N and nostocarboline.
Selective construction of alkaloid scaffolds by alcohol-based direct and mild aerobic oxidative Pictet-Spengler reactions
Han, Feng,Li, Huan,Liu, Haicheng,Liu, Jianping,Xu, Qing
supporting information, p. 7079 - 7085 (2020/10/02)
Employing TBN/TEMPO as the catalysts and oxygen as the oxidant, the biologically and pharmaceutically significant tetrahydro-β-carboline and β-carboline alkaloid scaffolds that used to be obtained by multi-step processes can now be selectively obtained in only one-stepviadirect aerobic oxidative Pictet-Spengler reactions of tryptamines with alcohols under mild conditions, with water generated as the byproduct. In this reaction, TBN/TEMPO was interestingly found to be able to facilitate the cyclization step of the whole reaction. This method tolerates a variety ofC- andN-substituted tryptamines, and both the more reactive benzylic and allylic alcohols and the less reactive aliphatic alcohols. This method can also be extended to dihydro-β-carboline synthesis and applied to the more available and more economical tryptophan for β-carboline synthesis, revealing its broad substrate scope and potential in synthetic applications.
Organic base-promoted efficient dehydrogenative/decarboxylative aromatization of tetrahydro-β-carbolines into β-carbolines under air
Zhao, Ziquan,Sun, Yan,Wang, Lilin,Chen, Xuan,Sun, Yanpei,Lin, Long,Tang, Yulin,Li, Fei,Chen, Dongyin
supporting information, p. 800 - 804 (2019/02/16)
Organic base DBN has been identified as an efficient reagent for promoting the dehydrogenative/decarboxylative aromatization of tetrahydro-β-carbolines under air atmosphere, to access the corresponding β-carbolines in moderate to good yields. The utility of this protocol for the gram-scale synthesis of β-carboline alkaloids eudistomin U (7) and harmane (10) has also been demonstrated.
Green synthesis method for beta-carboline heterocyclic compounds
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Paragraph 0056; 0057; 0058; 0059, (2018/09/11)
The invention discloses a green synthesis method for beta-carboline heterocyclic compounds. The green synthesis method includes that the beta-carboline heterocyclic compounds are made of alcohols compounds, oxidative condensation, cyclization and re-oxidation one-pot cascade reaction is carried out on tryptamines compounds and alcohol in oxygen under the catalytic effects of catalysts TEMPO and catalysts TBN to obtain the beta-carboline heterocyclic compounds, the reaction temperatures range from 40 DEG C to 120 DEG C, and the reaction time ranges from 6 hours to 48 hours. The green synthesismethod has the advantages that inexpensive, easily available, stable and low-toxicity alcohols which can come from wide sources are used as the raw materials for the beta-carboline heterocyclic compounds, the aerobic oxidative condensation, cyclization and re-oxidation cascade reaction is carried out on the tryptamines compounds and the alcohol under the synergistic catalytic effects of the catalysts TEMPO and the catalysts TBN and acetic acid solvent conditions to prepare the beta-carboline heterocyclic compounds, target products are high in selectivity, a byproduct is water, and accordinglythe green synthesis method is high in efficiency and free of pollution.
Dehydrogenation of 1-aryl(hetaryl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acids and their esters with dimethyl sulfoxide
Abramyants,Lomov,Zavyazkina
, p. 1610 - 1615 (2017/01/28)
Oxidative dehydrogenation of 1-aryl(hetaryl)-1,2,3,4-tetrahydro-9Н-β-carboline-3-carboxylic acids derivatives with dimethyl sulfoxide leads to the formation of 1-aryl(hetaryl)-9Н-β-carbolines. Simultaneously with the dehydrogenation decarboxylation occurs
β-Carbolines as specific inhibitors of cyclin-dependent kinases
Song, Yongcheng,Wang, Jian,Teng, Su Fern,Kesuma, Djohan,Deng, Yu,Duan, Jinao,Wang, Jerry H.,Qi, Robert Zhong,Sim, Mui Mui
, p. 1129 - 1132 (2007/10/03)
Harmine (3), 7-fluoro-1-methyl β-carboline (35) and 1-(5-methyl-imidazol-4-yl) β-carboline (41) were potent and specific inhibitors of cyclin-dependent kinases. The degree of aromaticity of the tricyclic ring and the positioning of substituents are important for inhibitory activity. While most β-carbolines inhibited CDK2 and CDK5 to the same extent, selective inhibition against CDK2 was observed in 1-(2-chlorophenyl)- (12), 1-(2-fluorophenyl)- (15), and 1-(2-chloro-5-nitrophenyl)- (28) β-carbolines.
