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, 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, Organic
Nan-Fang Mo, Ying Zhang, Zheng-Hui Guan
Summary: An asymmetric organocatalyzed three-component Povarov reaction has been developed to construct azaspirocycles. A chiral phosphoric acid catalyst with a unique structure was highly efficient in the reaction, leading to a wide range of azaspirocycles in high yields and excellent enantioselectivities. This reaction has expanded the scope of the traditional Povarov reaction.
Article
Chemistry, Multidisciplinary
Zhi-Chen Wu, K. N. Houk, Dale L. Boger, Dennis Svatunek
Summary: This study investigates the reaction mechanism of 1,2,3-triazines and 1,2,3,5-tetrazine with amidines, revealing that the reaction proceeds through an addition/N-2 elimination/cyclization pathway. Contrary to previous expectations, the rate-limiting step in this transformation is the initial nucleophilic attack of amidines on azine C4.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Yang Lu, Meng-Meng Xu, Zhi-Mao Zhang, Junliang Zhang, Quan Cai
Summary: The study presented a copper-catalyzed asymmetric IEDDA reaction for the synthesis of six-membered carbocycles, leading to the successful asymmetric total syntheses of cephanolides A and B.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Li Huang, Ying Han, Jing Sun, Qiu Sun, Chao-Guo Yan
Summary: The base promoted tandem annulation reaction of activated cyclic 1,3-dipolarophiles with functionalized furo[2,3-d]pyrimidine-2,4-diones provided efficient synthetic protocols for complex dispiro/dispiro fused tricyclic compounds. This reaction proceeded via sequential ring-opening, formal [3 + 2] cycloaddition, and annulation processes.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Applied
Yi-Jun Jo, Muhammad Gulfam, Sung-Han Jo, Yeong-Soon Gal, Chul-Woong Oh, Sang-Hyug Park, Kwon Taek Lim
Summary: Researchers developed stimuli-responsive hydrogels based on hyaluronic acid and diselenide cross-linker for controlled drug release. These hydrogels exhibited rapid drug release under acidic, reducing, oxidizing, and NIR irradiation conditions, and showed good cytocompatibility and anti-tumor effect.
CARBOHYDRATE POLYMERS
(2022)
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
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)
Review
Chemistry, Organic
Abolfazl Olyaei, Mahdieh Sadeghpour
Summary: Furopyrimidine derivatives, especially furo[2,3-d]pyrimidine, are important heterocyclic compounds in pharmaceutical discovery research. They can be synthesized by constructing a furan ring on a pyrimidine derivative or generating the pyrimidine ring on a functionalized furan ring. Barbituric acids are commonly used as starting materials for the synthesis of these compounds through multicomponent reactions. This review aims to compile the literature on synthetic procedures for barbituric acid-based furo[2,3-d]pyrimidine and spirofuro[2,3-d]pyrimidines.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Sravya Gundala, Albert F. Khasanov, Dmitry S. Kopchuk, Ekaterina S. Starnoskaya, Yaroslav K. Shtaitz, Alexey P. Krinochkin, Eugeny B. Gorbunov, Grigory V. Zyryanov, Venkatapuram Padmavathi, Oleg N. Chupakhin
Summary: The study investigates the interactions of 5,6-diaryl-3-(quinolin-2-yl)-1,2,4-triazines with arynes. 2-(3,4-Diarylisoqunolin-1-yl)quinolines are obtained in up to 65% yield through the inverse-demand Diels-Alder reaction between 5,6-diaryl-3-(quinolone-2-yl)-1,2,4-triazines and benzyne, generated in situ.
POLYCYCLIC AROMATIC COMPOUNDS
(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)
Review
Chemistry, Multidisciplinary
Salvador Mastachi-Loza, Tania I. Ramirez-Candelero, Luis J. Benitez-Puebla, Aydee Fuentes-Benites, Carlos Gonzalez-Romero, Miguel A. Vazquez
Summary: Chalcones are aromatic ketones that have a wide range of biological activity and are biogenetic precursors of other important molecules. Due to their structural diversity and ease of synthesis, they are often used as building blocks for chemical transformations. They can participate in nucleophilic additions and Diels-Alder reactions, and novel methodologies have been developed for [4+2] cycloadditions using chalcones as electron systems.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Applied
Manon Genet, Abdelilah Takfaoui, Jerome Marrot, Christine Greck, Xavier Moreau
Summary: A series of enantioenriched 4,5,6,7-tetrahydrofuro[2,3-b]pyridines were synthesized using a cycloisomerization/cycloaddition strategy, with yields ranging from 27% to 90% and high levels of stereoselectivity. Sequential relay catalysis with a gold complex and a diphenylprolinol silyl ether was successfully applied to a combination of diversely functionalized substrates.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
