Article
Chemistry, Multidisciplinary
Pedro Brandao, Carolina S. Marques, Elisabete P. Carreiro, M. Pineiro, Anthony J. Burke
Summary: Multicomponent reactions (MCRs) are a valuable tool in diversity-oriented synthesis, gaining relevance in the fields of organic and medicinal chemistry. Isatin, with its unique reactivity, can undergo different MCRs to afford various interesting scaffolds, including oxindole-derivatives and heterocyclic compounds resulting from ring-opening reactions. New methodologies have been developed for the application of this easily available starting material in MCRs in recent years.
Article
Chemistry, Organic
Ze-Liang He, Peng Chen, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: A cascade assembly method for synthesizing 1,2,3,4-tetrahydrodibenzo[b,d]-furan architectures incorporating a spirooxindole motif has been developed with moderate to good yields and excellent diastereoselectivity. Fused indole analogues can similarly be obtained by employing benzylideneacetones with an o-TsNH group.
Article
Chemistry, Organic
Muniyappa Vijaykumar, Chandini Pradhan, Rajesh G. Gonnade, Benudhar Punji
Summary: The palladium-catalyzed chemoselective oxygenation of C(sp2)-H and C(sp3)-H bonds in substituted isatin derivatives is described. This mild protocol allows for the C5 C(sp2)-H oxygenation of isatins through electrophilic intermolecular C-H palladation in concentrated solutions using PhI(OAc)2 or Selectfluor as an oxidant, while the N-CH3 C(sp3)-H oxygenation is achieved in dilute solutions via carbonyl-assisted intramolecular palladation in the presence of K2S2O8. This oxygenation reaction provides a direct and unified approach for synthesizing diverse oxygenated isatins with sensitive functionalities, including biorelevant compounds.
Article
Chemistry, Organic
Hongchen Li, Lidong Shan, Chulong Liu, Nan Liu, Xinyan Wang, Yuefei Hu
Summary: A novel method for chemospecific C3- and C2-olefinations of isatins using TfOH-promotion has been developed, presenting the first examples of Grob fragmentation with isatins and amides as substrates.
Article
Chemistry, Applied
Soroor Torfi-Zadegan, Foad Buazar, Mohammad Hosein Sayahi
Summary: This study presents a novel approach utilizing marine diatom extract to produce distinctive SnO2 nanoparticles with organic components derived from marine sources. These nanoparticles serve as highly effective catalysts in ultrasound-assisted reactions, resulting in the synthesis of various organic products with remarkable efficiency and the ability to be reused.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhipeng Zhang, Li Jing, Er-Qing Li, Zheng Duan
Summary: The study achieved (4 + 1) annulations of isatin derivatives with [2-(hydroxymethyl)allyl] carbonates using a cooperative palladium/P(NEt2)(3) system, leading to an extensive library of highly structurally diverse spirooxindole derivatives.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Jindian Duan, Yiyang Mao, Anmei Xian, Binsen Rong, Gaochen Xu, Zhenjiang Li, Lili Zhao, Ning Zhu, Kai Guo
Summary: A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, providing valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity. The reaction involves Cu(I) initiated multiple steps, featuring mild reaction conditions and broad substrate scope. DFT calculations demonstrated that the [3+2] annulation pathway is energetically favorable both in kinetics and thermodynamics.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Medicinal
Liming Wang, Zhe Chen, Huiting Jiang, Jie Zhang, Ying Jin
Summary: An organocatalytic enantioselective Friedel-Crafts alkylation of alpha-naphthols with isatin derivatives was successfully catalyzed by Takemoto-type urea catalyst, giving high yields (75%-92%) and excellent enantiomeric excess (up to 95% ee) of the resulting 3-(naphthalen-2-yl)-3-hydroxy-2-oxindoles. The scope of the catalyst and substrate was expanded in this methodology.
Article
Chemistry, Organic
Dan Liu, Jing Sun, Qiu Sun, Chao-Guo Yan
Summary: An efficient synthetic protocol for the selective construction of spiro[indoline-3,5'-pyrrolo[3,4-b]azepines] and spiro[indoline-3,3'-pyrroles] via a cycloaddition reaction has been successfully developed. The reaction involves the use of specific reagents to achieve high yields and diastereoselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Acoustics
Haiyan Zhu, Qinghui Wen, Sukhvir Kaur Bhangu, Muthupandian Ashokkumar, Francesca Cavalieri
Summary: High-frequency ultrasound can transform the antibiotic doxycycline into nanoparticles with antioxidant and antimicrobial properties. These nanodrugs can have controlled and multiple bio-functionalities.
ULTRASONICS SONOCHEMISTRY
(2022)
Article
Chemistry, Organic
Amrah Nasim, Gilian T. Thomas, Jeffrey S. Ovens, Stephen G. Newman
Summary: We report an intermolecular Ni-catalyzed reductive coupling reaction for the synthesis of 3-hydroxyoxindoles. Unlike common metal-mediated methods, sec-butanol is used as a mild reductant, resulting in benign waste products. This reaction is facilitated by a P2N2 ligand and proceeds through a modified carbonyl-Heck-type pathway.
Article
Chemistry, Organic
Souvik Guha, Satyanarayana Gadde, Naresh Kumar, David StClair Black, Subhabrata Sen
Summary: A series of telescoping methodologies were reported for the one-pot synthesis of biologically relevant β-carboline derivatives 6 and spiro[pyrrolidinone-3,3']indole 7. Careful optimization of the reaction sequence and conditions allowed for the exclusive access to compounds 6 and 7. Air oxidation of gamma-carbolinones 6 yielded aromatic gamma-carbolines 8.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Hongmin Qu, Yu Chen, Xiangling Ceng, Pei Tang, Huijing Wang, Fener Chen
Summary: The catalytic enantioselective alkynylation of isatins has been developed using a Zn(OCOCF3)(2)/chiral bis(sulfonamide)-diamine (BSDA) catalyst under mild conditions. The reaction produces chiral 3-alkynyl-3-hydroxy-2-oxindoles with moderate to excellent yields (up to 96%) and good to excellent enantioselectivities (up to 97% ee). The reaction is applicable to a broad range of aryl-substituted terminal alkynes and substituted isatins.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhi Tang, Zhiqing Wang, Zhihong Peng, Qinghua Yang, Shuang-Feng Yin, Renhua Qiu
Summary: An efficient protocol for synthesizing indolin-2-ones from benzofuranones and aryl amines using iodine as a mediator has been developed. A diverse range of benzofuranones and aryl amines undergo cross-dehydrogenative coupling and amidation to produce products in yields ranging from 24-93%. The reaction can be easily scaled-up to produce indolin-2-ones in a gram scale, with further chemical manipulation enabling useful transformations of the phenol ring.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Seyyed Mohammad Ebrahimi, Ali Kareem Abbas, Hossein Shahbazi-Alavi, Javad Safaei-Ghomi, Atefeh Bakhtiari, Raheleh Teymuri
Summary: Functionalized SBA-15 has been utilized as an efficient catalyst for the preparation of spiroindolines, offering advantages such as catalyst reusability, low loading, high yields in short reaction times, easy product separation, and the use of ultrasonic irradiation as a valuable and powerful technology. Characterization of the catalyst was conducted using various techniques, including XRD, FE-SEM, TEM, EDX, XPS, FT-IR, N-2 adsorption analysis, TPD, and TGA.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Chemistry, Organic
Mozhgan Esfandiari, Ali Kareem Abbas, Hossein Shahbazi-Alavi, Javad Safaei-Ghomi
Summary: CeO2/CuO@nitrogen graphene quantum dots@NH(2) nanocomposite has been utilized as an efficient catalyst for the synthesis of benzodiazepines through multi-component reactions. This method offers experimental simplicity, a wide range of products, short reaction times, reusability of the catalyst, and low catalyst loading.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Chemistry, Organic
Javad Safaei-Ghomi, Yahya Fazeli-Mehrabani, Ali Kareem Abbas, Hossein Shahbazi-Alavi
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
(2020)
Article
Chemistry, Multidisciplinary
Mozhgan Esfandiari, Ali Kareem Abbas, Mohammad Reza Vakili, Hossein Shahbazi-Alavi, Javad Safaei-Ghomi
Summary: The study utilized chitosan functionalized by triacid imide as a catalyst for synthesizing benzodiazepines, with the catalyst structure confirmed through multiple analysis methods. The experimental findings showed that this method offers benefits such as short reaction times, ease of operation, a wide range of products, and catalyst recyclability.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Chemistry, Organic
Mohammad Sadegh Dehghan-Manshadi, Ali Kareem Abbas, Mozhgan Esfandiari, Hossein Shahbazi-Alavi, Javad Safaei-Ghomi
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
(2021)
Article
Chemistry, Multidisciplinary
Seyyed Mohammad Ebrahimi, Ali Kareem Abbas, Hossein Shahbazi-Alavi, Javad Safaei-Ghomi
Summary: Nano-CoAl2O4 has been utilized as an effective catalyst in the preparation of 5-oxo-2,5-dihydro-3 furancarboxylates through multi-component reactions. The method offers experimental simplicity, a wide range of products, high yields, recyclability of the nanocatalyst, and low catalyst loading as key features.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Chemistry, Organic
Hossein Shahbazi-Alavi, Ali Kareem Abbas, Javad Safaei-Ghomi
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
(2021)
Article
Chemistry, Multidisciplinary
Seyyed Mohammad Ebrahimi, Ali Kareem Abbas, Hossein Shahbazi-Alavi, Javad Safaei-Ghomi, Atefeh Bakhtiari, Raheleh Teymuri
Summary: Functionalized SBA-15 has been utilized as an efficient catalyst for the preparation of spiroindolines, offering advantages such as catalyst reusability, low loading, high yields in short reaction times, easy product separation, and the use of ultrasonic irradiation as a valuable and powerful technology. Characterization of the catalyst was conducted using various techniques, including XRD, FE-SEM, TEM, EDX, XPS, FT-IR, N-2 adsorption analysis, TPD, and TGA.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Nanoscience & Nanotechnology
Javad Safaei-Ghomi, Ali Kareem Abbas, Marzieh Shahpiri
Article
Materials Science, Multidisciplinary
Reza Mohassel, Mahnaz Amiri, Ali Kareem Abbas, Azam Sobhani, Mahdi Ashrafi, Hossein Moayedi, Masoud Salavati-Niasari
JOURNAL OF MATERIALS RESEARCH AND TECHNOLOGY-JMR&T
(2020)
