Article
Chemistry, Organic
Pragati Biswal, Tanmayee Nanda, Namrata Prusty, Smruti Ranjan Mohanty, Ponneri C. Ravikumar
Summary: A rhodium-catalyzed oxidative C-H/N-H dehydrogenative[3 + 2] annulation strategy has been developed for the synthesis of 2-methylindole scaffolds by reacting anilines and N-allylbenzimidazole. This transformation involves the cleavage of the thermodynamically stable C-N bond of allylamine and proceeds through a cascade of C(sp(2))-H alkylation followed by intramolecular cyclization. Detailed mechanistic studies have been performed to identify a key intermediate.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Bo Wang, Minyan Li, Gui Gao, Alvaro Sanz-Vidal, Bing Zheng, Patrick J. Walsh
Summary: An efficient synthesis method for tryptamines has been developed using 2-iodoaryl allenyl amines and radical cyclization reactions to construct indole structures. The utility and versatility of this method are demonstrated by the successful synthesis of 22 tryptamine derivatives in high yields. The formation of indoles is accompanied by the in situ removal of the Boc protecting group.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Jagannath Rana, Palaniyappan Nagarasu, Murugan Subaramanian, Akash Mondal, Vedichi Madhu, Ekambaram Balaraman
Summary: The general and efficient C(alpha)-alkylation of oxindoles with unactivated secondary alcohols as alkylating agents catalyzed by a newly developed NNN-Mn(II) complex demonstrates the importance of the NH moiety in the complex and M-L cooperation during the catalytic transformation.
Article
Chemistry, Organic
Takashi Mino, Toshiki Yamaoka, Kohei Watanabe, Chihiro Masuda, Shohei Kasano, Yasushi Yoshida, Ryo Takita, Yoshio Kasashima, Masami Sakamoto
Summary: P,olefin ligand/palladium catalyst systems can easily afford the corresponding 2-substituted 3-allylindole derivatives in good to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mingqin Zhao, Xinyan Li, Xiaoyu Zhang, Zhihui Shao
Summary: The catalytic dehydrogenation of alcohols is crucial for sustainable production of valuable products, providing a new strategy for green organic synthesis in chemical industries. This study introduces a manganese-based catalytic system that efficiently synthesizes C3-alkylated indoles from benzyl alcohols and indoles via the borrowing hydrogen process. Furthermore, dehydrogenative coupling of 2-arylethanols and indoles yields C3-alkenylated indoles. Additionally, reacting 2-aminophenethanol instead of indoles under the same conditions also yields the corresponding indole products with high selectivity.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Xi Xiao, Xiaobiao Lu, Ming Zhang, Haoqing Hou, Changfeng Wan, Jinbiao Liu
Summary: A novel synthetic method was successfully developed for the preparation of multisubstituted dihydrochromeno[2,3-b]indole derivatives in moderate to high yields using a catalytic environmentally benign iron salt.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Lin Huang, Jia-Hao Xie, Yue Cai, Chao Zheng, Xue-Long Hou, Li-Xin Dai, Shu-Li You
Summary: This study presents a novel N-alkylation of pyrroles through an Ir-catalyzed asymmetric allylic dearomatization-induced selective ring-expansive migration, providing a series of tetrahydropyrrolo[1,2-c]pyrimidine derivatives with good yields and excellent enantioselectivity. The proposed reaction mechanism is supported by DFT calculations and the characterization of the key intermediate.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Elvira R. Zaitseva, Dmitrii S. Ivanov, Nadezhda S. Baleeva, Alexander Yu. Smirnov, Andrey A. Mikhaylov, Mikhail S. Baranov
Summary: A new operationally simple single step method has been developed for the synthesis of indole-2-carboxylates from 2-dimethylaminobenzaldehydes and nitroacetic acid esters, with yields ranging from 22% to 59%.
Article
Chemistry, Organic
Biao Guo, Jiaying Lv, Le Lu, Ruimao Hua
Summary: A novel method for constructing the cyclopenta[c]quinoline ring has been developed, which involves the cyclization of 3-bromoindoles with internal alkynes in the presence of palladium. The mechanism of the formation of the cyclopenta[c]quinoline ring is proposed to proceed via a double [1,5] carbonsigmatropic rearrangement of the spirocyclic cyclopentadiene intermediate, generated from the cyclization of 3-bromoindoles with internal alkynes. This study also presents a new ring-expansion reaction of the pyrrole ring to pyridine via one carbon insertion into the C2-C3 bond of indoles, providing a simple and distinct route for constructing tricyclic fused-quinoline derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Bei Zhang, Jian-Qing Qi, Yuhan Liu, Zhipeng Li, Jian Wang
Summary: In this study, a novel NHC and photo-co-catalyzed alkylacylation of olefins using diazo esters as radical source is reported, presenting a new idea for transient radical generation with the only byproduct being N-2. Compared to previous methods, this process shows great atom economy with reduced discard fragments.
Article
Chemistry, Organic
Qiwen Gao, Liuting Luo, Chen Chen, Kangmei Wen, Zhibo Zhu, Xiaodong Tang
Summary: The direct utilization of amines for C-C bond formation without prefunctionalization remains a significant challenge. In this study, a base-promoted deaminative coupling of gramines with aminomalaimides under redox-neutral conditions was reported. A series of indolmethyl-substituted aminomaleimides that emitted fluorescence were synthesized in good-to-excellent yields. Biological evaluation revealed that some products exhibited antiproliferative activity against human cancer cell lines.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Shao-Bai Yan, Rui Wang, Zha-Gen Li, An-Na Li, Chuanyong Wang, Wei-Liang Duan
Summary: This paper reports a Cu-catalyzed asymmetric C(sp(2))-H arylation using diaryliodonium salts, which enables the synthesis of a range of chiral phosphonic diamides and chiral phosphine oxide indoles with high selectivity under mild conditions.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Leiqing Fu, Yunyun Liu, Jie-Ping Wan
Summary: The study reported the synthesis of NH-free pyrroles via Pd-catalyzed annulation of enaminones and alkenes, activating multiple C-H bonds and producing a variety of products, with the interesting observation of hydrogen gas evolution during the reactions.
Article
Chemistry, Organic
Shun Zhou, Hui-Ling Qian, Jian-Qiang Zhao, Yong You, Zhen-Hua Wang, Jun-Qing Yin, Yan-Ping Zhang, Ming-Feng Chen, Wei-Cheng Yuan
Summary: A formal [4 + 2] cycloaddition reaction between 3-nitroindoles and ortho-aminophenyl p-quinone methides was developed through a dearomatization process. This method provides an efficient approach for the synthesis of tetrahydro-5H-indolo[2,3-b]quinolones with satisfactory results. The use of bifunctional Cinchona alkaloid-squaramide as the catalyst enabled the asymmetric version of the reaction, leading to the formation of chiral products with moderate to good enantioselectivities. This work represents the first dearomative cycloaddition of electron-deficient heteroarenes triggered by aza-Michael addition from p-QMs.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Liang-Hua Zou, Biao Liu, Cheng Wang, Zeyu Shao, Junqi Zhou, Andong Shao, Jian Wen
Summary: An efficient and green method for synthesizing various alkyl amines through the cleavage of vinylsulfonium salts' C(sp(3))-S bond has been developed. This reaction can be conducted under air atmosphere and shows a broad range of applicability with N-nucleophiles. Additionally, N-vinylazoles can be obtained with moderate to good yields through the reaction of vinylsulfonium salts with N-containing heterocycles in the presence of a base at room temperature.
ORGANIC CHEMISTRY FRONTIERS
(2022)
