- Synthesis of Thiazoles and Isothiazoles via Three-Component Reaction of Enaminoesters, Sulfur, and Bromodifluoroacetamides/Esters
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A three-component strategy for the synthesis of thiazoles and isothiazoles has been developed by employing enaminoesters, fluorodibromoiamides/ester, and sulfur. The thiazoles and isothiazoles were formed via two C-F bond cleavages along with the formation of new C-S, C-N, and N-S bonds. The strategy provides high selectivity for the synthesis of thiazoles/isothiazoles, which have vital applications in drug discovery and development.
- Ma, Xingxing,Yu, Xiaoxia,Huang, Hua,Zhou, Yao,Song, Qiuling
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supporting information
p. 5284 - 5288
(2020/07/14)
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- Cu-Catalyzed Denitrogenative Transannulation of 3-Aminoindazoles to Assemble 1-Aminoisoquinolines and 3-Aminobenzothiophenes
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We disclose a novel Cu-catalyzed denitrogenative transannulation of 3-aminoindazoles to afford diverse functionalized 3-aminobenzothiophenes and 1-aminoisoquinolines, in which denitrogenative transannulation of 3-aminoindazoles is reported for the first t
- Zhou, Yao,Wang, Ya,Lou, Yixian,Song, Qiuling
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supporting information
p. 8869 - 8873
(2019/09/12)
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- Divergent Synthesis of Multisubstituted Unsymmetric Pyrroles and Pyrrolin-4-ones from Enamino Esters via Copper-Catalyzed Aerobic Dimerization
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A facile synthetic method to access multisubstituted unsymmetric pyrrole and pyrrolin-4-one derivatives is disclosed. In the presence of Cu(OAc)2 and KOAc, substituted pyrrole derivatives are produced in good yields (up to 93 %) through oxidative cyclization of enamino esters. Meanwhile, using CuCl2 and TFA (trifluoroacetic acid), pyrrolin-4-one derivatives are obtained in excellent yields (up to 94 %) through 1,2-aryl migration. A wide range of functional groups have been tolerated, and a reliable method for the synthesis of valuable multisubstituted pyrroles and pyrrolin-4-ones has been developed.
- Chen, Zhi-Wei,Zheng, Lei,Liu, Jin
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p. 3051 - 3060
(2019/05/24)
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- Structural insight into the optimization of ethyl 5-hydroxybenzo[g]indol-3-carboxylates and their bioisosteric analogues as 5-LO/m-PGES-1 dual inhibitors able to suppress inflammation
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The release of pro-inflammatory mediators, such as prostaglandines (PGs) and leukotrienes (LTs), arising from the arachidonic acid (AA) cascade, play a crucial role in initiating, maintaining, and regulating inflammatory processes. New dual inhibitors of 5-lipoxygenase (5-LO) and microsomal prostaglandin E2 synthase-1 (mPGES-1), that block, at the same time, the formation of PGE2 and LTs, are currently emerged as a highly interesting drug candidates for better pharmacotherapie of inflammation-related disorders. Following our previous studies, we here performed a detailed structure-based design of benzo[g]indol-3-carboxylate derivatives, disclosing several new key factors that affect both enzyme activity. Ethyl 2-(3,4-dichlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate (4b, RAF-01) and ethyl 2-(3,4-dichlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate (7h, RAF-02) emerged as the most active compounds of the series. Additionally, together with selected structure based analogues, both derivatives displayed significant in vivo anti-inflammatory properties. In conclusion, modeling and experimental studies lead to the discovery of new candidate compounds prone to further developments as multi-target inhibitors of the inflammatory pathway.
- Bruno, Ferdinando,Errico, Suann,Pace, Simona,Nawrozkij, Maxim B.,Mkrtchyan, Arthur S.,Guida, Francesca,Maisto, Rosa,Olga?, Abdurrahman,D'Amico, Michele,Maione, Sabatino,De Rosa, Mario,Banoglu, Erden,Werz, Oliver,Fiorentino, Antonio,Filosa, Rosanna
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p. 946 - 960
(2018/07/24)
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- Copper-Catalyzed Tandem Reaction of Enamino Esters with ortho-Halogenated Aromatic Carbonyls: One-Pot Approach to Functionalized Quinolines
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An efficient and practical approach for the synthesis of functionalized quinolines has been developed by using the copper-catalyzed tandem C–C bond formation and C–N coupling reaction of enamino esters and ortho-halogenated aromatic carbonyl compounds. Various functional groups were tolerated under the reaction conditions, and a series of quinolines were easily obtained in moderate to good yields. A gram-scale reaction was also performed to demonstrate a further application of this synthetic method.
- Peng, Fei,Liu, Jin,Li, Lili,Chen, Zhiwei
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supporting information
p. 666 - 672
(2018/02/14)
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- Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane
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Catalytic asymmetric reduction of N-unsubstituted β-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted β-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of β-aryl- and β-alkyl-substituted free β-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.
- Ye, Jianheng,Wang, Chao,Chen, Lin,Wu, Xinjun,Zhou, Li,Sun, Jian
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supporting information
p. 1042 - 1047
(2016/04/19)
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- IBX mediated reaction of β-enamino esters with allylic alcohols: A one pot metal free domino approach to functionalized pyridines
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IBX facilitated the reaction of β-enamino esters with allylic alcohols affording a direct, one-pot and metal free synthesis of functionalized pyridines including 2-substituted nicotinic acids, densely substituted pyridines and precursors of azafluorenones. The methodology also afforded the racemic pyridine core of cyclothiazomycin.
- Gade, Narendar Reddy,Devendram,Pal, Manojit,Iqbal, Javed
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supporting information
p. 7926 - 7928
(2013/09/02)
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