Article
Chemistry, Organic
Chayamon Chantana, Jaray Jaratjaroonphong
Summary: In this study, unsymmetrical bis(indolyl)methane and 3-alkylindole derivatives were efficiently synthesized using FeCl3·6H2O as a catalyst for nucleophilic substitution reactions. The reaction conditions were mild, and the strategy showed advantages in terms of operational ease, cost-effectiveness, environmentally-friendly catalyst, broad functional group tolerance, and scalability.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Wangyu Li, Dungai Wang, Xiao Liang, Zhixiong Jin, Shiwen Zhou, Guanru Chen, Yuanjiang Pan
Summary: A Lewis acid-catalyzed selective reaction for the synthesis of diarylmethanes or oxoimidazolidines from anilines and glyoxylates was developed. The reaction yielded a series of aniline-based diarylmethanes and stereoselective oxoimidazolidines, depending on the catalyst used.
Article
Chemistry, Organic
Meng-Yang Chang, Chun-Yi Lin, Shin-Mei Chen
Summary: A high-yield, open-vessel route for the facile-operational, gram-scale synthesis of functionalized triarylmethanes (TRAMs) is described via silica-coated magnetic nanoparticles of modified polyphosphoric acid (NiFe2O4@SiO2-PPA)-mediated intermolecular Friedel-Crafts reaction of substituted aryl aldehydes with 2 equivalents of oxygenated arenes under environmentally friendly reaction conditions. Only water was generated as the by-product throughout the reaction process.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Sanjay Singh, Sankalan Mondal, Nagaraju Vodnala, Chinmoy Kumar Hazra
Summary: In this study, unsymmetrical polyarylated alkanes were synthesized using a cheap, commercially available Bronsted acid-catalytic system (pTSA center dot H2O)/HFIP. The one-pot three-component approach avoided the use of pyrophoric reagents, metal catalysts, toxic solvents, or Grignard reagents, and showed high greenness in terms of various green metrics. The method was also applied for the synthesis of pharmaceuticals and natural product functionalization.
Article
Chemistry, Organic
Shoko Nagahata, Seiya Takei, Satoshi Ueno
Summary: In this study, gamma-phenyl-beta,gamma-unsaturated ketones were synthesized in situ and reacted with alpha,beta-unsaturated carbonyls to form tri- or diarylated benzophenones in a one-pot manner.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hirotsugu Suzuki, Fumito Sasamori, Takanori Matsuda
Summary: In this study, we developed a rhodium-catalyzed alkoxylcarbonylation/acylation method using anhydrides as the carbonyl source to synthesize C7-carbonylated indolines. This catalytic process is additive- and CO-free, and it successfully achieves the C-H acylation of indolines, leading to the formation of alpha-branched ketones that were difficult to prepare using previously reported analogous catalytic reactions.
Article
Chemistry, Organic
Zhengyu Han, Wenlong Wang, Han Zhuang, Jie Wang, Cheng Wang, Jianhao Wang, Hai Huang, Jianwei Sun
Summary: This article describes an organocatalytic enantioselective formal hydro-arylation of 2-vinyl indoles for the synthesis of enantioenriched 2,3'-bis(indolyl)methanes bearing a quaternary carbon stereocenter. The reaction conditions are mild, the catalyst loading is low, and the efficiency and enantioselectivity are excellent. The resulting products exhibit promising anticancer activity.
Article
Chemistry, Applied
Meng-Yang Chang, Nai-Chen Hsueh
Summary: Here, we describe the Bi(OTf)(3)-catalyzed Friedel-Crafts-type annulation of sulfonyl o-hydroxyacetophenones with benzofused cycloethers. This single-step strategy produces functionalized dibenzofused medium-size (9-12) oxacycles through the formation of carbon-carbon and carbon-oxygen single bonds. The oxidative application of the resulting oxacycles is also investigated and the chemical structures of the key products are determined using single-crystal X-ray analysis. Water is generated as a byproduct in the overall process.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Biochemistry & Molecular Biology
Qi Li, Xiu-Xia Liang, Wang Zhang, Man-Yi Han
Summary: A novel double Friedel-Crafts reaction of acylsilanes in water is reported, which allows for the synthesis of bis(indolyl)methane derivatives with 1-hydroxy or 1-silyl substituents in moderate to high yield. The selectivity of the reaction is regulated by the hydrogen bonds in the 5-hydroxyindole, leading to the synthesis of 1-hydroxy-bis(indolyl)methane derivatives.
Article
Chemistry, Organic
Velu Saravanan, Arasambattu K. Mohanakrishnan
Summary: A one-pot synthesis of aryl- and heteroaryl-annulated carbazoles was achieved from 2/3-bromomethylindoles, along with a bis-domino reaction of 2,5-bis(bromomethyl)pyrrole with selected heteroarenes. The synthesized thienocarbazoles and thienodibenzofurans were successfully utilized for a second-generation domino reaction.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Anton A. Merkushev, Diana A. Eshmemet'eva, Maxim G. Uchuskin
Summary: A FeCl3-catalyzed protocol was developed for the Friedel-Crafts alkylation of 2-substituted furans with 2-nitrobenzhydrols, yielding 2-(2-nitrobenzyl)furans in good to high yields. The obtained product has demonstrated synthetic utility for the synthesis of substituted oxazino[2,3-a]indole.
Article
Chemistry, Organic
Sandra-L. Aranzazu, Alexis Tigreros, Andres Arias-Gomez, Jhon Zapata-Rivera, Jaime Portilla
Summary: An operably simple microwave-assisted BF3-mediated acetylation reaction of pyrazolo[1,5-a]pyrimidines has been reported. The synthesis of this essential building block is achieved in high yields using mild reaction conditions, inexpensive reagents, and even substrates with electron-deficient or highly hindered groups. The discovered acetylation method was successfully applied in other pi-excedent (N-hetero)aromatic substrates as well.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zi-Hao Jia, Ling-Yan Chen, Hao Zheng, Zhang-Rui Li, Qing-Chun Song, Ya Li
Summary: The study presents a successful synthesis of a series of chiral diarylmethylamines through the BINOL-derived DSI-catalyzed enantioselective aza-Friedel-Crafts reaction. The reaction provides a useful protocol for the direct synthesis of diarylmethylamine derivatives with good yields and excellent enantioselectivities (up to 97% ee).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Fang Lv, Jing Xiao, Junchun Xiang, Fengzhe Guo, Zi-Long Tang, Li-Biao Han
Summary: For the first time, H3PO3 was utilized as both the reducing reagent and the promotor in reductive benzylation reactions with aryl aldehydes. The combination of H3PO3/I-2 enabled various aromatic aldehydes to undergo iodination reactions and Friedel-Crafts type reactions with arenes, easily producing benzyl iodides and diarylmethanes in good yields while also leading to intramolecular cyclization reactions to give corresponding cyclic compounds. This novel strategy offers advantages of easy-handling, low-cost, and metal-free conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Yanshun Li, Mengqi Dong, Nanxing Gao, Guorui Cao, Dawei Teng
Summary: A zinc complex of a new spiroQuinox ligand with a spirocarbon stereogenic center was used for asymmetric Friedel-Crafts alkylation of indoles with cyclic N-sulfonyl ketimino esters. This catalytic system allows for facile synthesis of benzosultam derivatives functionalized with indole substituents, with high yield and excellent enantioselectivity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Nanoscience & Nanotechnology
Ponnaboina Thirupathi, Joo-Young Park, Lok Nath Neupane, Mallela Y. L. N. Kishore, Keun-Hyeung Lee
ACS APPLIED MATERIALS & INTERFACES
(2015)
Article
Chemistry, Analytical
Ponnaboina Thirupathi, Lok Nath Neupane, Keun-Hyeung Lee
ANALYTICA CHIMICA ACTA
(2015)
Article
Biochemistry & Molecular Biology
Munipally Praveen Kumar, Venu Sankeshi, R. Ravindar Naik, P. Thirupathi, Biswanath Das, T. N. Raju
CHEMICO-BIOLOGICAL INTERACTIONS
(2015)
Article
Biochemistry & Molecular Biology
Ponnaboina Thirupathi, Keun-Hyeung Lee
BIOORGANIC & MEDICINAL CHEMISTRY
(2013)
Article
Chemistry, Medicinal
Ponnaboina Thirupathi, Keun-Hyeung Lee
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2013)
Article
Chemistry, Multidisciplinary
Ponnaboina Thirupathi, Lok Nath Neupane, Keun-Hyeung Lee
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2012)
Article
Chemistry, Organic
Ponnaboina Thirupathi, Ponnaboina Saritha (nee Gudelli), Keun-Hyeung Lee
ORGANIC & BIOMOLECULAR CHEMISTRY
(2014)
Article
Chemistry, Organic
Mi-Hwa Yang, Ponnaboina Thirupathi, Keun-Hyeung Lee
Article
Chemistry, Organic
Sujung Jang, Ponnaboina Thirupathi, Lok Nath Neupane, Junho Seong, Hyunsook Lee, Wan In Lee, Keun-Hyeung Lee
Article
Chemistry, Multidisciplinary
N. Venkatagiri, T. Krishna, P. Thirupathi, K. Bhavani, C. K. Reddy
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
(2018)
Article
Chemistry, Organic
Santosh T. Kadam, Ponnaboina Thirupathi, Sung Soo Kim
SYNTHESIS-STUTTGART
(2011)
Article
Chemistry, Analytical
Lok Nath Neupane, Ponnaboina Thirupathi, Sujung Jang, Min Jung Jang, Jung Hwa Kim, Keun-Hyeung Lee
Article
Chemistry, Organic
Ponnaboina Thirupathi, Lok Nath Neupane, Keun-Hyeung Lee
Article
Chemistry, Multidisciplinary
Ponnaboina Thirupathi, Noole Venkatagiri, Chepyala Krishna Reddy
Article
Chemistry, Multidisciplinary
Songyi Han, Kwan Ho Jung, Lok Nath Neupane, Ponnaboina Thirupathi, Keun-Hyeung Lee
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2015)