Article
Chemistry, Organic
Bipin Kumar Behera, Sudip Shit, Subhamoy Biswas, Anil K. Saikia
Summary: An efficient methodology for the synthesis of di- and trisubstituted thiazol-2(3H)-ones from N-propargylamines and silver(I) trifluoromethanethiolate has been developed. The reaction proceeds through [3,3]-sigmatropic rearrangement/5-exodig cyclization of N-propargylamines. The starting material can be easily prepared via the A3-coupling reaction of amines, aldehydes, and alkynes. The methodology can also be extended to the synthesis of thiozole-2(3H)thione derivatives, and the photophysical properties of some synthesized compounds have been studied.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhenwei Lv, Yan Li, Erik V. Van der Eycken, Lingchao Cai, Liangliang Song
Summary: In this study, a metal-free cascade cyclization method was developed for the construction of structurally novel polyheterocycles. The approach involves the use of a hypervalent iodine(iii) reagent and generates diverse N-O fused spiro polyheterocycles in high yields. The synthesized compounds exhibit good antifungal activity against crop and forest pathogenic fungi, with one compound showing superior performance compared to the positive control.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Zhenwei Lv, Yan Li, Erik V. Van der Eycken, Lingchao Cai, Liangliang Song
Summary: Here, we report a metal-free cascade cyclization reaction that constructs structurally novel polyheterocycles by utilizing a hypervalent iodine(III) reagent. Under ambient conditions, alkyne-tethered N-alkoxybenzamides undergo a 6-exo-dig cyclization/dearomatization process to generate diverse N-O fused spiro polyheterocycles in good to high yields. This method features short reaction times, broad substrate scope, easy handling, and shows promising antifungal activity against crop and forest pathogenic fungi.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Tales A. C. Goulart, Ana M. S. Recchi, Davi F. Back, Gilson Zeni
Summary: The Lewis acid-promoted cyclization reaction of benzomidazole thiols with propargyl alcohols for the selective synthesis of benzoimidazolo thiazines and benzothiazolo imidazoles is described. The reaction is regioselective and controlled by the choice of solvent. The best reaction conditions were determined through systematic study, resulting in the formation of six-membered benzoimidazolo thiazines using boron trifluoride etherate and dichloromethane as the solvent, and five-membered benzothiazolo imidazoles using the same starting material and reagents with dimethylformamide as the solvent. The proposed mechanism of the cyclization reaction is based on experimental results and control experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Multidisciplinary Sciences
Kemiao Hong, Yi Zhou, Haoxuan Yuan, Zhijing Zhang, Jingjing Huang, Shanliang Dong, Wenhao Hu, Zhi-Xiang Yu, Xinfang Xu
Summary: This study reports a Rh-catalyzed reaction for the direct synthesis of furan-fused cyclobutanone compounds. DFT calculations reveal the reaction mechanism and the importance of using less reactive catalysts for high selectivity. This method allows the synthesis of previously inaccessible and unknown versatile synthetic blocks, while exhibiting anticancer activity.
NATURE COMMUNICATIONS
(2023)
Correction
Chemistry, Multidisciplinary
Hassan Seyrani, Sorour Ramezanpour, Aref Vaezghaemi, Farzad Kobarfard
Summary: The correction presents a novel reaction sequence for the selective synthesis of saccharin substituted 2,5-dihydropyrroles via sequential Ugi-Smiles reaction and transition-metal-free endo-dig Conia-ene cyclization.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Maryam Tajik, Morteza Shiri, Faiq H. S. Hussain, Yazdanbakhsh Lotfi Nosood, Behnaz Baeiszadeh, Zahra Amini, Rahman Bikas, Anna Pyra
Summary: An efficient base-mediated/metal-free approach was developed for the synthesis of 1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-3-carboxamide derivatives via intramolecular indole N-H alkylation of novel bis-amide Ugi-adducts. The main highlight of this study is the practical and highly regioselective preparation of new polycyclic functionalized pyrazino derivatives. This system is facilitated by Na2CO3 mediation in DMSO and 100 & DEG;C conditions.
Article
Chemistry, Organic
Ding Ma, Deshen Kong, Chenyang Wang, Khai-Nghi Truong, Kari Rissanen, Carsten Bolm
Summary: Treatment with Cs2CO3 allows S-methyl-N-ynonylsulfoximines to undergo 5-exo-dig cyclizations to form three-dimensional heterocycles. The reactions proceed at ambient temperature with a wide range of substrates, resulting in good to excellent yields of the corresponding products.
Article
Chemistry, Applied
Youpeng Zuo, Xinwei He, Qiang Tang, Wangcheng Hu, Tongtong Zhou, Wenbo Hu, Yongjia Shang
Summary: A cascade intramolecular 5-exo-dig cyclization of N-(2-iodophenyl)propiolamides and sequential amination/etherification protocol has been developed for the synthesis of amino- and phenoxy-substituted 3-methyleneindolinones using inexpensive Pd(PPh3)(4) as catalyst. The protocol allows for the assembly of oxindole cores with moderate functional group tolerance, providing a broad spectrum of products with diverse substituents in good to excellent yields.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Roberto do Carmo Pinheiro, Luiz Eduardo Welter, Bernardo A. Iglesias, Davi F. Back, Luiza Souza Marques, Cristina Wayne Nogueira, Gilson Zeni
Summary: Heterocycles fused to seven-membered rings were synthesized in a highly selective manner using potassium tert-butoxide-catalyzed one-pot cyclization. Systematic study revealed that a catalytic amount of potassium tert-butoxide, dimethyl sulfoxide, and the tert-BuOK/tert-BuOH equilibrium played crucial roles in the formation of products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yong-Hao Wang, You-Qin Jiang, Yun-Qian Zhang, Yong Ling, Liang Ming, Gong-Qing Liu
Summary: A dual catalytic approach combining photocatalyst and selenium-p-acid synergy has been used for the cyclization of N-propargylamides. This method offers a convenient access to oxazole aldehydes without using chemical oxidants, using low catalyst loadings, and utilizing air as a terminal and gratuitous oxidant. The reaction is applicable to various substrates, including aryl and alkyl propargyl amides, and can be used for the late-stage functionalization of drug molecules containing amides. Mechanistic studies indicate that the acridinium catalyst is capable of oxidizing diselenide and generating singlet oxygen (O-1(2)), which is responsible for this transformation.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Dakoju Ravi Kishore, Gedu Satyanarayana
Summary: This study presents an efficient and straightforward strategy for the synthesis of 2,3-disubstituted benzo[b]furans. The synthetic process involves a series of reactions, including a domino intermolecular coupling and intramolecular cyclization, resulting in a wide variety of compounds with good functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xinwei He, Demao Wang, Yanan Liu, Mengdi Wu, Yangzilin Kong, Qiang Tang, Yiping Wang, Chenli Fan, Yongjia Shang
Summary: A facile method for the synthesis of furan fused heterocyclic compounds has been developed using a regioselective cascade reaction. This reaction involves multiple steps and allows the formation of highly sterically congested products. The strategy described is easily scalable and allows for further synthetic transformations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Xiao-Biao Yan, Lun Li, Wen-Qiang Wu, Lun Xu, Ke Li, Yu-Cheng Liu, Hang Shi
Summary: The authors demonstrate a method to add alkanes with an amino functionality to olefins using a nickel catalyst that utilizes the amine itself as the hydride source, eliminating the need for an external hydride reagent. This approach allows for the production of valuable, complex structural motifs and chiral alpha-branched amines in organic synthesis. Additionally, the use of a P-chiral ligand further enhances the catalytic efficiency of the reaction.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Chao Liu, Liangliang Song, Vsevolod A. Peshkov, Erik V. Van der Eycken
Summary: A novel method utilizing a combination of Ugi-4CR and sequential C-S/C-N bond cleavage has been developed to prepare diverse peptidomimetics containing a primary amide in a rapid, efficient, and cost-effective manner. The approach demonstrates high yield, excellent chemoselectivity, and tolerance towards various functional groups. Compounds derived from pharmaceuticals and beta-amino acids were successfully prepared, suggesting a new direction for peptidomimetic synthesis.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Inorganic & Nuclear
Robabeh Moghadami, Esmail Vessally, Mirzaagha Babazadeh, Moosa Es'haghi, Ahmadreza Bekhradnia
JOURNAL OF CLUSTER SCIENCE
(2019)
Article
Environmental Sciences
S. M. Khadivi, L. Edjlali, A. Akbarzadeh, K. Seyyedi
INTERNATIONAL JOURNAL OF ENVIRONMENTAL SCIENCE AND TECHNOLOGY
(2019)
Article
Chemistry, Physical
Navid Salehi, Ladan Edjlali, Esmail Vessally, Ibon Alkorta, Moosa Es'haghi
COMPUTATIONAL AND THEORETICAL CHEMISTRY
(2019)
Correction
Chemistry, Physical
Navid Salehi, Ladan Edjlali, Esmail Vessally, Ibon Alkorta, Moosa Es'haghi
COMPUTATIONAL AND THEORETICAL CHEMISTRY
(2019)
Article
Pharmacology & Pharmacy
Mohamad Kazempour, Ladan Edjlali, Abolfazl Akbarzadeh, Soodabeh Davaran, Sima Shahmohammadi Farid
JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY
(2019)
Review
Chemistry, Multidisciplinary
Wanxi Peng, Esmail Vessally, Sattar Arshadi, Aazam Monfared, Akram Hosseinian, Ladan Edjlali
TOPICS IN CURRENT CHEMISTRY
(2019)
Article
Chemistry, Physical
Samireh Gohari, Ladan Edjlali, Esmail Vessally, Moosa Es'haghi, Moein Goodarzi
COMPUTATIONAL AND THEORETICAL CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Zahra Rahmani, Ladan Edjlali, Esmail Vessally, Akram Hosseinian, Parvaneh Delir Kheirollahi Nezhad
JOURNAL OF SULFUR CHEMISTRY
(2020)
Article
Chemistry, Applied
Zhila Zare-Akbari, Siavoush Dastmalchi, Ladan Edjlali, Leila Dinparast, Moosa Es'haghi
APPLIED ORGANOMETALLIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Zahra Rahmani, Ladan Edjlali, Esmail Vessally, Akram Hosseinian, Parvaneh Delir Kheirollahi Nezhad
JOURNAL OF SULFUR CHEMISTRY
(2020)
Article
Materials Science, Multidisciplinary
Soheila Mohamadian-Kalhor, Ladan Edjlali, Hadi Basharnavaz, Moosa Es'haghi
Summary: The aluminum fumarate metal-organic framework showed high inhibition efficiency as a corrosion inhibitor for AM60B magnesium alloy, with the performance improving with increasing inhibitor concentration. The proposed MOF demonstrated great potential with an inhibition efficiency of 88.35% at 400 ppm.
JOURNAL OF MATERIALS ENGINEERING AND PERFORMANCE
(2021)
Article
Biochemistry & Molecular Biology
Behlol Hashemzadeh, Ladan Edjlali, Parvaneh Delir Kheirollahi Nezhad, Esmail Vessally
Summary: The study showed that hexa-cata-hexabenzocoronene nanographene (HCHN) is a promising anode material for Mg-ion batteries (MIBs) due to its high storage capacity, strong ion mobility, and large cell voltage.
JOURNAL OF MOLECULAR MODELING
(2021)
Article
Chemistry, Multidisciplinary
Fatemeh Gharibzadeh, Esmail Vessally, Ladan Edjlali, Moosa Es'haghi, Robab Mohammadi
IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION
(2020)
Article
Chemistry, Multidisciplinary
Bahman Ramezani, Gholam Hossein Shahverdizadeh, Ladan Edjlali, Fatemeh Ramezani, Mirzaagha Babazadeh