Article
Biochemistry & Molecular Biology
Maria Paola Bracciale, Guhyun Kwon, Dongil Ho, Choongik Kim, Maria Laura Santarelli, Assunta Marrocchi
Summary: Organic semiconductors are emerging as viable alternatives for cost-effective (opto)-electronic devices due to their advantages in simple deposition, low thermal budgets, and compatibility with flexible substrates. In this study, we report the optimized synthesis and characterization of a helically shaped polycyclic aromatic compound, benzopentahelicene-3,6-dione, and demonstrate its potential in the fabrication of organic field effect transistors.
Article
Chemistry, Multidisciplinary
Mark A. Maskeri, Anthony J. Fernandes, Giovanni Di Mauro, Nuno Maulide, K. N. Houk
Summary: This study investigates the competition between Claisen-type reaction and (2+2) cyclization of Keteniminium ions through a combination of density functional theory and experimental investigations. The calculations reveal a small difference in the free energy barrier between the two reactions. Further investigations probe the electronics of the substrate and a competing side reaction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Kentaro Kawai, Kazuki Ikeda, Akane Sato, Akira Kabasawa, Masahiro Kojima, Kenta Kokado, Akira Kakugo, Kazuki Sada, Tatsuhiko Yoshino, Shigeki Matsunaga
Summary: Dynamic covalent bonds are useful tools, but their applications are limited by the activation conditions. This study reports the dynamic covalent bonding properties of 1,2-disubstituted 1,2-dihydro-1,2,4,5-tetrazine-3,6-dione and its hetero-Diels-Alder reactions at room temperature.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Chen Yan, Jing Sun, Ying Han, Chao-Guo Yan
Summary: The Diels-Alder reactions of 2-(1-alkylindol-3-yl)naphthalene-1,4-diones and 3-phenacylideneoxindoles catalyzed by p-TsOH showed fascinating diastereoselectivity, resulting in trans-isomers under hydrated conditions and cis-isomers under anhydrous conditions. Additionally, the reactions of 2-(indol-3-yl)naphthalene-1,4-diones with 3-arylideneindolin-2-ones and 2-arylidene-1,3-indanediones also displayed interesting cis/trans selectivity, yielding various spiro[indoline-3,6'-naphtho[2,3-c]carbazoles].
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mitra Sanie, Ehsan Zahedi, Seyed Hosein Ghorbani, Ahmad Seif
Summary: The kinetic and thermodynamic parameters of the Newman-Kwart rearrangement were evaluated using Minnesota density functionals with the aug-cc-pVTZ basis set and compared with benchmark results. The study showed excellent agreement between the evaluated parameters and experimental data, with topological and chemical events occurring during the reaction process.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Mallepalli Shankar, Adula Kalyani, Mandala Anitha, Alla Siva Reddy, K. C. Kumara Swamy
Summary: In this study, phosphorus-based naphthalenes were synthesized through a series of reactions. Using Pd(OAc)2 as a catalyst, alpha-aryl allenylphosphonates or allenylphosphine oxides were self-dimerized and cyclized. Additionally, a [Pd] complex was obtained by reacting allenylphosphine oxides with Pd(OAc)2 in the presence of PPh3/Ag2CO3, and it could be used as a catalyst for C-C bond-forming reactions of phosphorus-based allenes with 2-iodophenol. Densely substituted 3,6-diphenylpyridazines were successfully synthesized through a thermally induced regioselective Inverse Electron Demand Diels-Alder (IEDDA) reaction and a [1,3]-H shift.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xu-Heng Yang, Jian Huang, Fang Wang, Zhuoliang Liu, Yujiao Li, Cheng-an Tao, Jianfang Wang
Summary: A synthetic strategy based on sequential application of aza-Claisen rearrangement, C-H functionalization, C-N coupling, and cyclization has been developed for the synthesis of various medium-sized N-heterocycles of pharmaceutical relevance, providing a highly efficient synthesis of N-heterocycles of different ring sizes in moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Chaofan Wang, Ling Fang, Zhiyong Wang
Summary: The study reports a base-induced reaction for synthesizing tetrahydro-1,2,4-triazine derivatives, which involves the cycloaddition of two in situ generated reactive intermediates.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Dong-Chao Wang, Jia-Hui Liu, Yu-Qing Guan, Hai-Ming Guo
Summary: A direct dearomative [4 + 2] annulation of electron-poor N-heteroarenes with azoalkenes generated in situ from alpha- halogeno hydrazones was developed under mild conditions, leading to the synthesis of fused polycyclic tetrahydro-1,2,4-triazines with potential biological activity in high yields (up to 96%). Various alpha-halogeno hydrazones and N-heteroarenes were successfully used in this reaction, demonstrating the broad applicability of this method.
Review
Chemistry, Organic
Md. Belal, Santa Mondal, Sabina Yashmin, Abu Taleb Khan
Summary: 4-Hydroxydithiocoumarin is a versatile organic precursor with various reactive sites, capable of producing important heterocycles and other organic compounds. Under oxidative conditions, it can also form unusual bonds, expanding its applications in organic synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yaroslav K. Shtaitz, Aluru Rammohan, Alexey P. Krinochkin, Evgeny D. Ladin, Ilya I. Butorin, Nataliya N. Mochulskaya, Igor A. Khalymbadzha, Pavel A. Slepukhin, Vadim A. Shevyrin, Dmitry S. Kopchuk, Grigory V. Zyryanov, Oleg N. Chupakhin
Summary: A solvent-free reaction between C6-unsubstituted 5-aryl-1,2,4-triazines and 2-amino-4-aryloxazoles at high temperature was studied. The reaction proceeds via inverse electron demand aza-Diels-Alder reaction and shows highly regioselective formation of 3,6-diarylpyridines in up to 60% isolated yield. The synthetic approach demonstrates valuable advantages of high regioselectivity and solvent-free conditions.
Article
Chemistry, Multidisciplinary
Alexey P. Krinochkin, Mallikarjuna R. Guda, Aluru Rammohan, Dmitry S. Kopchuk, Igor L. Nikonov, Evgeny D. Ladin, Sougata Santra, Ilya N. Egorov, Grigory V. Zyryanov, Oleg N. Chupakhin
Summary: This article reports the reaction between 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines, which forms hardly available 2-amino-3,6-di(het)aryl-pyridines through aza-Diels-Alder autoclave reaction. The reaction yields up to 67% after two steps and 75% in one-pot synthesis, making the obtained compounds promising for medicinal chemistry.
MENDELEEV COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Xunhua Wang, Jianfeng Yang, Ruifeng Lv, Pengfei Song, Denghui Ye, Jitian Liu, Xiaoxun Li
Summary: This study discloses a palladium-catalyzed cycloaddition strategy that achieves high selectivity and yield. The method is capable of constructing complex molecules with specific stereostructures, and the products can be further transformed into other chiral compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
A. Rammohan, Ya. K. Shtaitz, E. D. Ladin, A. P. Krinochkin, P. A. Slepukhin, V. V. Sharutin, E. R. Sharafieva, T. A. Pospelova, D. S. Kopchuk, G. V. Zyryanov
Summary: The solvent-free reaction between 3,6-diaryl-1,2,4-triazine-5-carbonitriles and 2-amino-4-aryloxazoles was investigated, leading to the formation of 3- and 4-aryl-substituted pyridines in yields up to 20% and 27%, respectively. This reaction differs from the reaction of 3-(2-pyridyl)-1,2,4-triazine-5-carbonitriles with the same substrates. Therefore, 2-amino-4-aryloxazoles function as synthetic analogues of arylacetylenes in this case.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
(2023)
Article
Crystallography
Zeliha Atioglu, Mehmet Akkurt, Gunay Z. Mammadova, Sixberth Mlowe
Summary: In the cation of the title salt, the four tetrahydrofuran rings adopt envelope conformations are linked by dimeric C H...O hydrogen bonds, forming a three-dimensional network structure with the anions. The crystal packing is mainly contributed by H...H, C...H/H...C, O...H/H...O, and F...H/H...F interactions, according to Hirshfeld surface analysis.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
(2021)
