Article
Chemistry, Organic
Kailas V. Preeti, Kailas V. Kallurkar, Prathama S. Mainkar, Raju Adepu, Srivari Chandrasekhar
Summary: A concise route for the synthesis of dihydrobenzo-[j]-phenanthridinones has been developed using an aryne annulation strategy under metal-free reaction conditions. The reaction involves multiple C-C and C-N bond cleavages/formations through Diels-Alder reaction, aromatization-driven C-N bond cleavage, and amide formation.
Article
Chemistry, Organic
Matteo Lanzi, Racha Abed Ali Abdine, Maxime De Abreu, Joanna Wencel-Delord
Summary: This study reported the synthesis of dissymetric 2,3,2',3',4-substituted biaryls via pericyclic reactions of cyclic diaryl lambda(3)-bromanes. The method provides functional group tolerance and atom economy, allowing access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for scale-up, while postfunctionalizations have been developed leveraging the residual Br-atom.
Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A Yb(OTf)(3)-catalyzed formal (4 + 3) cycloaddition reaction was successfully achieved using donor-acceptor cyclopropanes and 3-benzylideneindoline-2-thiones as reactants. Functionalized 5,10-dihydro-2H-thiepino[2,3-b]indole derivatives were synthesized with good yields and moderate to good diastereoselectivity. This reaction represents the first (4 + 3) cycloaddition of 3-benzylideneindoline-2-thiones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yuchen Du, Joel T. Mague, Robert A. Pascal
Summary: Highly congested derivatives of biphenyl were prepared through double Diels-Alder reactions, sometimes resulting in only one addition and in other cases leading to two additions. The structures of the compounds showed crowding but without the distortions seen in previous observations.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Julia O. Strelnikova, Alexander N. Koronatov, Nikolai Rostovskii, Alexander F. Khlebnikov, Olesya Khoroshilova, Mariya A. Kryukova, Mikhail S. Novikov
Summary: The domino reaction catalyzed by Rh-2(Piv)(4) leads to the formation of N-sulfonylated (Z)-2-(2-aminovinyl)imidazoles, providing a direct and flexible access to the desired compounds.
Article
Chemistry, Multidisciplinary
Masao Ohashi, Dan Tan, Jiayan Lu, Cooper S. Jamieson, Daiki Kanayama, Jiahai Zhou, K. N. Houk, Yi Tang
Summary: The synthesis of cis-decalin structures using [4 + 2] cycloaddition with high stereoselectivity is challenging. In this study, we investigated the biosynthetic pathway of the fungal natural product fischerin (1) and identified a novel pericyclase, FinI, which catalyzes this reaction. The cocrystal structure of FinI, a predicted O-methyltransferase, with the product and SAM provides valuable insights into the natural formation of cis-decalin.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Manashi Sarmah, Deep Jyoti Das, Dhiraj Dutta, Rinku Baishya, Pranjal Gogoi
Summary: A Pd-catalyzed method for the direct synthesis of benzo[a]carbazoles from internal alkynes and N-tosyl-iodoindoles has been demonstrated. This method allows the synthesis of electronically different benzo[a]carbazoles with good yields. The synthesized compounds showed potent anticancer activity against human lung and breast cancer cells.
Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A new compound was synthesized successfully in this study by using Yb-(OTf)(3) catalyst to react donor-acceptor cyclopropanes with sulfur-containing 4π components. The reaction showed high yields and moderate to good diastereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Nanoscience & Nanotechnology
Yajing Huang, Songlin Chen, Ruitong Ma, Yalin Cheng, Lun Jin, Guohua Chen
Summary: A novel method has been developed to synthesize fine coal-based carbon composite particles with rich nitrogen-doped microcrystalline structure for superior electromagnetic-shielding performance. The occurrence of Diels-Alder (D-A) reaction between coal and FMA significantly changes the structure of coal, while ball-milling and heat treatment improve the structural integrity of the carbon networks, resulting in excellent electromagnetic shielding properties when mixed with paraffin.
ADVANCED COMPOSITES AND HYBRID MATERIALS
(2022)
Article
Chemistry, Organic
Gary L. Points, Christopher M. Beaudry
Summary: Substituted carbazoles are efficiently synthesized from 3-triflato-2-pyrones and alkynyl anilines, allowing for multiple substituents with complete control of regiochemistry, resulting in complex substitution patterns. This strategy can also be applied to prepare substituted bicarbazoles and related biaryls, and has been demonstrated in the synthesis of the carbazole natural product clausine C.
Article
Chemistry, Organic
Milauni M. Mehta, Jordan A. M. Gonzalez, James L. Bachman, Neil K. Garg
Summary: We present a method for constructing the core structure of the manzamine alkaloid keramaphidin B using a strain-promoted cycloaddition reaction. This method tolerates nitrile and primary amide functional groups, and can be followed by a retro-Diels-Alder reaction to increase structural complexity. These findings highlight the potential of strained cyclic allenes in building intricate structures, and provide inspiration for further studies on these transient intermediates.
Article
Chemistry, Organic
Po Yuan, Tanja Gaich
Summary: In this study, we reported a synthetic method for the enantioselective and convergent total synthesis of (+)-pepluanol A, a natural product with a structurally intriguing skeleton. The method achieved high diastereoselectivity and convergency through key reactions for constructing the unique framework.
Article
Chemistry, Multidisciplinary
Xia Chen, Cheng Zhong, Yuling Lu, Meng Yao, Zhenhua Guan, Chunmei Chen, Hucheng Zhu, Zengwei Luo, Yonghui Zhang
Summary: A practical and efficient method has been developed for the synthesis of fluorescent 2,3-naphthalimide derivatives via an intramolecular didehydro-Diels-Alder reaction. The methodology shows wide substrate scope, good functional group tolerance and practicality for gram-scale synthesis of environmentally sensitive fluorophores with shorter time, fewer steps and less waste disposal. Experimental and computational studies support the crucial role of the propiolimide moiety in the transformation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Liwei Zhao
Summary: A series of 9-position substituted triptycene derivatives were synthesized from 9-substituted anthracenes through key Diels-Alder reaction, with both benzoquinon and aryne studied as dienophile. The diastereomers of triptycene 10a were separated using chiral high-performance liquid chromatography (HPLC) column.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Anh Le, Daesung Lee
Summary: This study explores the substituent-dependent reactivity and selectivity in intramolecular reactions of arynes tethered with different allene isomers. It is found that the presence of 1,3-disubstituted allene favors an Alder-ene reaction over a [2 + 2] cycloaddition, while a 1,1-disubstituted allene prefers the [2 + 2] cycloaddition. Additionally, a 1,1,3-trisubstituted allene-tethered aryne shows preference for an Alder-ene reaction over a [2 + 2] cycloaddition.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Multidisciplinary
Tony Roy, Akkattu T. Biju
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Organic
Fabien Gelat, Thomas Poisson, Akkattu T. Biju, Xavier Pannecoucke, Tatiana Besset
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Santigopal Mondal, Arghya Ghosh, Subrata Mukherjee, Akkattu T. Biju
Article
Chemistry, Organic
Manas Das, Trinadh Kaicharla, Johannes F. Teichert
Review
Chemistry, Multidisciplinary
Santigopal Mondal, Santhivardhana Reddy Yetra, Subrata Mukherjee, Akkattu T. Biju
ACCOUNTS OF CHEMICAL RESEARCH
(2019)
Article
Chemistry, Organic
Arghya Ghosh, Atanu Patra, Subrata Mukherjee, Akkattu T. Biju
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Rahul N. Gaykar, Subrata Bhattacharjee, Akkattu T. Biju
Article
Chemistry, Physical
Tamal Kanti Das, Avik Ghosh, Kuruva Balanna, Pradipta Behera, Rajesh G. Gonnade, Udaya Kiran Marelli, Abhijit Kumar Das, Akkattu T. Biju
Article
Chemistry, Organic
Subrata Bhattacharjee, Avishek Guin, Rahul N. Gaykar, Akkattu T. Biju
Editorial Material
Chemistry, Multidisciplinary
Anup Bhunia
Article
Chemistry, Multidisciplinary
Kalipada Jana, Anup Bhunia, Armido Studer
Article
Chemistry, Organic
Nils L. Frye, Anup Bhunia, Armido Studer
Article
Polymer Science
David M. Guptill, Bhavani Shankar Chinta, Trinadh Kaicharla, Shu Xu, Thomas R. Hoye
Summary: Poly(ester-amide)s (PEAs) were prepared by reacting MVL-derived diamidodiols with diacid chlorides in solution, resulting in materials with plastic properties. The stiffness of the materials can be tuned by choosing appropriate precursors. NMR studies were used to detect the degradation products of these materials.
Article
Chemistry, Multidisciplinary
Trinadh Kaicharla, Birte M. Zimmermann, Martin Oestreich, Johannes F. Teichert
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Tony Roy, Rahul N. Gaykar, Subrata Bhattacharjee, Akkattu T. Biju
CHEMICAL COMMUNICATIONS
(2019)
