Article
Chemistry, Organic
Shrey P. Desai, Matthew T. Zambri, Mark S. Taylor
Summary: This paper describes a method for regioselective N-alkylation of various azole-type heterocycles using alkene or epoxide electrophiles. The activation of heterocyclic nucleophiles for selective N-functionalization is achieved by using diphenylborinic acid and an amine cocatalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Weidi Zeng, Hui Li, Duozhi Wang, Lei Zhou
Summary: A mild and convenient method for the synthesis of 3-trifluoromethylpyrroles via base-mediated [3 + 2] cycloaddition has been described. N-Acyl a-amino acids serve as 1,3-dipole precursors without the need for additional activating agents. The reaction exhibits a high level of regioselectivity, regardless of the electronic nature and size of the substituents on the 1,3-dipoles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Pavel S. Bobrov, Sergei D. Kirik, Ivan V. Peterson, Georgii A. Suboch
Summary: This article describes the efficient synthesis of novel nitroso-pyrazolylquinoxalines through regioselective cyclocondensation of 2-hydroxyimino-1,3-diketones with hydrazinylquinoxalines. The use of 2-hydroxyimino-1,3-diketones as electrophilic reagents in cyclocondensation with hetarylhydrazines is reported for the first time. The synthesis of nitroso-substituted pyrazolylquinoxalines was achieved in high yields using both one-pot and two-step procedures, and a gram-scale synthesis, as well as oxidation and reduction reactions, were successfully carried out.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Julia Altarejos, Estibaliz Merino, David Sucunza, Juan J. J. Vaquero, Javier Carreras
Summary: A facile one-pot (3 + 2) cycloaddition-isomerization-oxidation sequence using 2,2,2-trifluorodiazoethane and styryl derivatives has been developed for the synthesis of 5-aryl-3-trifluoromethylpyrazoles. The reaction showed broad functional group tolerance and high yields under mild conditions. DFT calculations confirmed the reactivity observed experimentally by analyzing the transition state energies of the cycloaddition reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Soumita Dwari, Partha Partim Nath, Chandan K. Jana
Summary: An unprecedented method for the synthesis of 1,3-diaryl 4-alkyl pyrazoles as a single regioisomer has been reported, which avoids the use of additional steps and hazardous oxidants.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Pengrui Jiang, Jingcheng Guo, Minghua Gong, Xiangui Zhou, Wei Cao, Zhenqian Fu, Wei Huang
Summary: A novel N-heterocyclic carbene-catalyzed annulation reaction of bromoenals with 2-aminochromones has been successfully developed, leading to the efficient synthesis of structurally diverse chromeno[2,3-b]pyridinones in acceptable to excellent yields. The reaction features mild conditions, a broad substrate scope, and easy scalability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Haifeng Yu, Kehua Wang, Xue Zhang, Wenju Wang
Summary: The efficient method developed allows for complementary and regioselective synthesis of isomeric 3-(isoxazol-5-yl)indoles and 3-(isoxazol-3-yl)indoles through the regioselective cyclocondensation reaction, with good yields achieved using different conditions.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Applied
Meng-Yang Chang, Nai-Chen Hsueh
Summary: Herein, a metal triflates-catalyzed one-pot domino cyclocondensation reaction of 1,3-bis-sulfonylacetones and 3-arylacroleins via (3+3) or (3+2+1) annulation has been proposed to construct diversified 2-sulfonyl-4-arylphenols and 2,6-bis-sulfonyl 5-aryl-4-arylidene-2-cyclohexenones. In this efficient reaction, C-C and C=C bonds are formed through a cascade process, and 3-arylacrolein acts as a C3 and C1 synthon during the formation of a six-membered ring system under mild conditions. The plausible mechanism has been proposed and discussed.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Yu-Ting Tian, Fa-Guang Zhang, Jun-An Ma
Summary: A regioselective [3 + 2] cyclo-addition reaction of 3-alkynoates with Seyferth-Gilbert reagent was developed with the trigger of Et3N to produce a series of trisubstituted pyrazole-3-phosphonates. A one-pot cycloaddition/alkylation sequence was further utilized to access the fully substituted pyrazoles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Mina Ding, Eunjin Cho, Zhihao Chen, Sang-Wook Park, Tae-Hoon Lee
Summary: In this study, the effects of EPZ compounds, PRMT5 inhibitors, on RANKL-induced osteoclast differentiation were investigated. EPZ015866 attenuated osteoclast differentiation more effectively than EPZ015666. The compounds inhibited the nuclear translocation of NF-kappa B, preventing osteoclast differentiation and bone resorption. EPZ015866 may be a potential drug candidate for the treatment of osteoporosis.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Alejandro Gonzalez-Benjumea, Dolores Linde, Juan Carro, Rene Ullrich, Martin Hofrichter, Angel T. Martinez, Ana Gutierrez
Summary: Research on epoxide metabolites from n-3 and n-6 polyunsaturated fatty acids has shown that fungal unspecific peroxygenases can convert these fatty acids into mono-epoxides with high regio- and enantioselectivity. Specifically, Agrocybe aegerita and Collariella virescens enzymes demonstrated 91% conversion rates with strict regioselectivity. This study highlights the potential synthetic utility of fungal peroxygenases in fatty acid epoxidation.
Article
Chemistry, Multidisciplinary
Rohit Kumar, Diksha Parmar, Devesh Chandra, Sarthi, Upendra Sharma
Summary: The Rh(iii)-catalysed C(sp(3))-H bond amidation of 8-methylquinolines using N-hydroxyphthalimides as the amidation source is explored. Diversely substituted 8-methylquinolines were well tolerated and furnished the amidated products in excellent yields with high regioselectivity. The developed reaction conditions were also applied successfully for the secondary C(sp(3))-H amidation of 8-ethylquinolines, showing its applicability in gram-scale synthesis and product diversification.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Yingying Zhang, Yating Huang, Kewei Yu, Xiaoxiang Zhang, Wenhua Yu, Jiale Tang, Yiran Tian, Wanxing Wei, Zhuan Zhang, Taoyuan Liang
Summary: Herein, we report a novel iron and iodine cooperative catalytic system for the synthesis of diverse 2-amino-3-alkylindoles. The method exhibits good substrate and functional group compatibility, and the catalyst system and feedstocks are readily available, showing great potential for further exploration of biological activities.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Amu Wang, Ya-Zhou Liu, Zhongke Shen, Zeen Qiao, Xiaofeng Ma
Summary: A TEMPO-mediated [3 + 2] annulation-aromatization protocol for the preparation of pyrazolo[1,5-a]pyridines has been developed, offering good to excellent yields with high and predictable regioselectivity. The modification of marketed drugs and a one-pot three-step gram scale synthesis of a key intermediate for Selpercatinib preparation have been demonstrated.
Article
Chemistry, Organic
Suresh Kumar Yadav, Masilamani Jeganmohan
Summary: A redox-neutral [4 + 2] annulation of N-chlorobenzamides/acrylamides with substituted alkenes using Co(III) catalyst at ambient temperature is demonstrated. The reaction provides pharmaceutically important 3,4-dihydroisoquinolinone derivatives in good yields, preserving the synthetically useful functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
