Article
Chemistry, Organic
Alexander N. Koronatov, Kseniia K. Afanaseva, Pavel A. Sakharov, Nikolai V. Rostovskii, Alexander F. Khlebnikov, Mikhail S. Novikov
Summary: A new method for the synthesis of 1-alkyl-3-sulfonamido-1H-pyrroles via the Rh(ii)-catalyzed denitrogenative coupling of two different types of 1,2,3-triazoles has been developed. The reaction mechanism involves the attack of the rhodium-bound azavinyl carbene, leading to the formation of metal-free ylides and subsequent conversion to the desired products. This protocol provides high yields of 3-sulfonamidopyrroles, demonstrating promising synthetic applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Leiyang Lv, Ge Gao, Yani Luo, Kuantao Mao, Zhiping Li
Summary: The study developed a three-component assembly method under transition-metal-free and open-air conditions for the construction of various 5-amino NH-1,2,3-triazoles, offering a simple and widely applicable approach. It was also demonstrated that NH-1,2,3-triazoles can be smoothly converted to regiospecific N-2 alkylated 1,2,3-triazole products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Naimish K. Verma, Smritilekha Bera, Rajesh Gonnade, Dhananjoy Mondal
Summary: The copper-catalyzed oxidative azide-olefin cycloaddition (OAOC) reaction provided an efficient method for preparing biologically active 1,4,5-trisubstituted 1,2,3-triazoles. The reaction exhibited great regioselectivity and resulted in the synthesis of diverse mono- and bis-(1,4,5-trisubstituted 1,2,3-triazole) functionalized heterocyclic compounds. XRD analysis confirmed the regioselectivity and stability of the method, and some derivatives showed promising antifungal properties.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Mahdieh Mohammad Karbasi, Zohreh Mirjafary, Hamid Saeidian, Javad Mokhtari
Summary: Novel 1,2,3-triazole-dithiocarbamate hybrids were synthesized in moderate to good yields using a green solvent system, and their structures were characterized by various techniques. DFT analysis was used to study some properties of the products, with the calculated data in close agreement with experimental data.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Biochemistry & Molecular Biology
Christopher R. Butler, Justin Bendesky, Allen Milton Schoffstall
Summary: Regioselective reactions are important in synthetic organic chemistry, as seen in the reduction of 1-substituted 1,2,3-triazole 4,5-diesters where the C(5) ester groups are more reactive and the presence of a beta-hydroxyl group on the N(1)-substituent enhances the reduction rate. The regioselectivity is attributed to lower electron densities in the C(5) and C(5) ester carbonyl carbon of the 1,2,3-triazole, especially in cases involving intramolecular hydrogen bonding.
Article
Chemistry, Multidisciplinary
Suguru Yoshida, Yuki Sakata, Yoshihiro Misawa, Takamoto Morita, Tomoko Kuribara, Harumi Ito, Yuka Koike, Isao Kii, Takamitsu Hosoya
Summary: Efficient consecutive formation of 1,2,3-triazoles using multiazide platforms has been achieved in this study. A four-step synthesis of tetrakis(triazoles) was successfully performed from a tetraazide platform molecule, based on the unique clickability of the 1-adamantyl azido group. This method was applied to the convergent synthesis of tetrafunctionalized probes in a modular synthetic manner.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Cong Guan, Jiabin Yin, Jian Ji, Jinhua Liu, Xiang Wu, Tong Zhu, Shunying Liu
Summary: A regioselective electrochemical C-H amination method using easily accessible ethers has been developed to synthesize N (2)-substituted 1,2,3-triazole. Multiple substituents, including heterocycles, were well-tolerated, and 24 examples were obtained in moderate to good yields. Control experiments and DFT calculations revealed that the electrochemical synthesis occurs through a N-tosyl 1,2,3-triazole radical cation process, promoted by single-electron transfer from the lone pair electrons of the aromatic N-heterocycle, and the desulfonation is responsible for the high N (2)-regioselectivity.
Article
Polymer Science
Shota Yamasaki, Yuri Kamon, Linlin Xu, Akihito Hashidzume
Summary: Through copper(I)-catalyzed and Huisgen cycloaddition reactions, 1,2,3-triazole polymers with different substituents were successfully synthesized. The crystalline properties of the polymers were influenced by the permittivity of the solvent and the type of substituents used. Additionally, the polymers exhibited fluorescence behavior in DMF, with the fluorescence peak shifting based on the excitation wavelength.
Article
Chemistry, Organic
Jose Laxio Arenas, Pascal Retailleau, Jean-Michel Gillet, Nour-Eddine Ghermani, Sandrine Ongeri, Benoit Crousse
Summary: The 5-fluoro triazole amino acid scaffold prepared by halogen exchange was successfully incorporated into peptides. The X-ray diffraction results revealed an important localization of the 5-fluoro triazole motif on one side of the negative potential surface, with the fluorine atom showing a cylindrical shape in its electron density deformation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Polymer Science
Jukka Niskanen, Mathieu N. Tousignant, Alexander J. Peltekoff, Benoit H. Lessard
Summary: 1,2,3-triazole based polyionic liquids have potential applications in organic electronics, with the ability to control their structure and charge to manipulate their properties. Substitution of inorganic counterions with organic counterions significantly improves the performance of metal-insulator-metal capacitors, enhancing their key performance metrics.
Article
Biochemistry & Molecular Biology
Zohreh Mirjafary, Mahdieh Mohammad Karbasi, Parsa Hesamzadeh, Hamid Reza Shaker, Asghar Amiri, Hamid Saeidian
Summary: A series of 1,2,3-triazole derivatives based on benzothiazole were synthesized using a simple and green method. The synthesized compounds showed promising anti-inflammatory and inhibition activities. ADMET analysis revealed two molecules with potential for drug development.
Article
Chemistry, Multidisciplinary
Menghan Cui, Changhui Su, Rong Wang, Qing Yang, Chunxiang Kuang
Summary: This novel and green route involves the direct synthesis of vinyl triazole derivatives with alkynes and triazoles promoted by an inorganic base under transition metal-free conditions, showing great catalytic activity for the anti-Markovnikov stereoselective hydroamination of alkynes. Good yields with excellent functional group tolerance are successfully achieved for a range of substrates, making it an advanced concept for the synthesis of alkenyl triazole with a versatile and cost-efficient approach.
Review
Chemistry, Applied
Gurleen Singh, Nancy George, Riddima Singh, Gurjaspreet Singh, Sushma, Gurpreet Kaur, Harminder Singh, Jandeep Singh
Summary: This review focuses on the 1,2,3-triazole-based sensor probes synthesized selectively by CuAAC, which have the ability to detect single or multiple ions under specific conditions. The review also discusses the techniques and sensing mechanisms involved in ion detection using chemosensor probes.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Dmitry B. Eremin, Valery V. Fokin
Summary: Water significantly impacts organic reactions by speeding them up or altering their selectivity. Performing reactions on-water provides a unique opportunity to influence chemical reactivity in complex environments. The on-water switch in the formation of triazoles controlled by the dual spray shows a change in chemoselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Optics
Islam H. El Azab, Adil A. Gobouri, Tariq A. Altalhi, H. S. El-Sheshtawy, N. Almutlaq, Hisham A. Maddah, M. Sh Zoromba, M. H. Abdel-Aziz, M. Bassyouni, A. Ibrahim, Asma Alanazy, Bakheet Awad Alresheedi, Ahmed F. Al-Hossainy
Summary: A novel active photosensitizer, 4MOTZ, was efficiently synthesized using click chemistry and showed promising optical properties, making it a potential candidate for future optoelectronic devices such as solar cells.
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)