Article
Chemistry, Multidisciplinary
Hamada Mohamed Ibrahim, Haider Behbehani
Summary: An efficient high-pressure-assisted trifluoroacetic acid-catalyzed protocol has been established for synthesizing unreported novel pyrido-triazine and pyrido-triazino-indole derivatives. The use of Q-tube reactor and trifluoroacetic acid was crucial for the success of the transformation, as X-ray single-crystal analysis was utilized to authenticate the structure of the synthesized products.
Article
Chemistry, Organic
Li-Wen Shen, Zhen-Hua Wang, Yong You, Jian-Qiang Zhao, Ming-Qiang Zhou, Wei-Cheng Yuan
Summary: An unprecedented (3+1) cyclization of alpha-nitro-sostyrenes, generated in situ from alpha-bromooximes, and N-tosyloxycarbamates was developed, enabling the synthesis of a range of structurally unique and hitherto unexplored 2,3-dihydrodiazete N-oxides in moderate to high yields. The products possess a highly strained four-membered ring structure containing two nitrogen atoms. The synthetic applicability of the products was also demonstrated by many important conversions to diverse nitrogen-containing compounds.
Article
Chemistry, Multidisciplinary
Luca De Angelis, Graham C. Haug, Gildardo Rivera, Soumen Biswas, Ammar Al-Sayyed, Hadi Arman, Oleg Larionov, Michael P. Doyle
Summary: One important reaction of 1,2,3-triazines is the inverse electron demand Diels-Alder (IEDDA) cycloaddition with a dienophile, which proceeds through nucleophilic addition to the triazine followed by N-2 loss and cyclization. Previous studies have not provided a comprehensive understanding of the site of nucleophilic addition on the triazine. This study investigated the C-, N-, H-, O-, and S-nucleophilic additions on 1,2,3-triazine and 1,2,3-triazine-1-oxide frameworks and revealed the differentiation of addition at the 4- and 6-positions. Computational studies further examined the factors influencing the outcomes of these reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Maria Papadopoulou, Edward C. Taylor
Summary: A method for preparing 2-aryl-2,3-dihydrothieno[2,3-b]pyridines is introduced, along with a one-pot synthesis of these compounds from thiosemicarbazide.
Article
Chemistry, Multidisciplinary
Jie Ouyang, Rajat Maji, Markus Leutzsch, Benjamin Mitschke, Benjamin List
Summary: Here, we report the design of a highly enantioselective, catalytic (4 + 3) cycloaddition reaction enabled by strong and confined IDPi Lewis acids. This reaction allows the synthesis of novel compounds with multiple stereocenters from gem-dialkyl 2-indolylalcohols and dienolsilanes. The method exhibits broad substrate scope and versatile downstream chemical modifications. Density functional theory-supported mechanistic studies reveal the significance of the in-situ generated silylium species in an overall concerted yet asynchronous cycloaddition.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Alexey P. Krinochkin, Yaroslav K. Shtaitz, Aluru Rammohan, Ilya I. Butorin, Maria Savchuk, Igor A. Khalymbadzha, Dmitry S. Kopchuk, Pavel A. Slepukhin, Vsevolod V. Melekhin, Anna Shcheglova, Grigory Zyryanov, Oleg N. Chupakhin
Summary: An operationally simple and highly efficient one-pot method has been developed for the synthesis of pyridines appended with pyrazole via an NH linker. The synthesized compounds showed promising in silico activity against JAK1, SYK, and FAK1 kinases. In vitro testing demonstrated significant cytotoxicity of the most promising compound against A-172 and HepG2 cancer cell lines, with IC50 values below 50 μM. The in vitro anticancer activity correlates well with the predicted in silico data.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hong Xu, Bei Wang, Fu-Yu Li, Ji-Yu Wang
Summary: A series of novel carbazolequinones were efficiently obtained through a B(C6F5)3-catalyzed [4 + 2] cyclization reaction. This method not only had a simple operation, broad substrate range, and high atomic economy, but also had a low catalyst loading and avoided using metal catalysts. In addition, diverse new carbazole-fused compounds were constructed under different reduction conditions. The photophysical characterization results showed that the structure of carbazole-fused derivatives had a significant impact on the fluorescence properties.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zhimei Mao, Aimin Huang, Lin Ma, Min Zhang
Summary: A facile visible light-promoted approach has been developed for the synthesis of anthracenone-furans from readily available 2,3-dibromonaphthoquinones and phenylbenzofurans via a formal Diels Alder reaction. This reaction involves wavelength-selective agitation of 4CzIPN, energy transfer to quinones, recombination of 1,6-biradicals, and elimination to give anthracenone-furans in good to excellent yields in one pot.
Article
Chemistry, Multidisciplinary
Divanshu Gupta, Alain Omont, Holger F. Bettinger
Summary: The carriers of diffuse interstellar bands (DIBs) are still largely unknown, but recent analysis indicates that n-acenes could be potential carriers of some DIBs, with dehydroacenes possibly forming after absorption of interstellar UV photons. The study suggests that the formation of cyclacenes from n-acenes after multiple absorption of UV photons is energetically conceivable.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biochemistry & Molecular Biology
Ekaterina A. Lystsova, Alexander S. Novikov, Maksim V. Dmitriev, Andrey N. Maslivets, Ekaterina E. Khramtsova
Summary: Acyl(imidoyl)ketenes can be used to synthesize diverse drug-like heterocycles. By utilizing the [4+2]-cyclodimerization of acyl(1,3-benzothiazol-2-yl)ketenes, a new synthetic approach to pharmaceutically interesting pyrido[2,1-b][1,3]benzothiazol-1-ones has been developed. Thermal analysis and computational studies revealed the suitability of 3-aroylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-triones as a source of acyl(1,3-benzothiazol-2-yl)ketenes, and a novel mode of thermal transformation of [e]-fused 1H-pyrrole-2,3-diones was discovered. The synthesized pyrido[2,1-b][1,3]benzothiazol-1-ones are of interest due to their potential antiviral activity.
Article
Chemistry, Organic
Yuhang Xue, Jianbo Gan, Naili Luo, Cunde Wang
Summary: In this study, a DABCO-promoted cyclization reaction of substituted 2-amino-4H-chromen-4-ones with substituted 2,6-dibenzylidenecyclohexan-1-ones was investigated. Under mild conditions, this reaction provided a novel and efficient access to the 7,8,9,10tetrahydro-12H-chromeno[2,3-b]quinolin-12-ones in good yields, with predominantly E-selective exocyclic double bond.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Bo Qin, Zhepei Lu, Yanxing Jia
Summary: We have successfully achieved the divergent total synthesis of four kopsane alkaloids, which share a complex heptacyclic caged ring system. Key transformations in this synthesis include an asymmetric Diels-Alder reaction for constructing the central bicyclo[2.2.2]octane moiety and the quaternary stereocenter at C20, a SmI2-mediated cascade reduction/aldol reaction for constructing the five-membered ring and the quaternary stereocenter at C7, and a late-stage cascade reductive amination/cyclization for establishing the highly strained caged ring system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Wei Cao, Yingchao Dou, Cyrille Kouklovsky, Guillaume Vincent
Summary: The first total synthesis of the monoterpene indole alkaloids ophiorrhine A is reported via a late stage bioinspired intramolecular Diels-Alder cycloaddition. The synthesis includes the construction of the indolopyridone moiety, cyclodehydration, and the desired spontaneous intramolecular Diels-Alder cycloaddition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xia Chen, Cheng Zhong, Yuling Lu, Meng Yao, Zhenhua Guan, Chunmei Chen, Hucheng Zhu, Zengwei Luo, Yonghui Zhang
Summary: A practical and efficient method has been developed for the synthesis of fluorescent 2,3-naphthalimide derivatives via an intramolecular didehydro-Diels-Alder reaction. The methodology shows wide substrate scope, good functional group tolerance and practicality for gram-scale synthesis of environmentally sensitive fluorophores with shorter time, fewer steps and less waste disposal. Experimental and computational studies support the crucial role of the propiolimide moiety in the transformation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Inorganic & Nuclear
Lorenzo Bonaldi, Marco Bortoluzzi, Stefano Zacchini, Guido Pampaloni, Fabio Marchetti, Lorenzo Biancalana
Summary: The chemistry of 1,2,4,5-tetrazines has attracted attention in the synthesis and application field. Recent studies have shown that regioselective reactions with alkynes and alkenes are favored when the tetrazine ring is coordinated to certain metal centers. This study explores the reactivity of tetrazines with chalcogenocyanate anions and demonstrates the formation of new heterocycles. The resulting ruthenium complexes were characterized using various analytical and spectroscopic techniques.
INORGANIC CHEMISTRY
(2023)
