Article
Chemistry, Multidisciplinary
Huy Tran, Guillaume Revol, Alyson Poyser, Louis Barriault
Summary: In this study, a novel Lewis acid gold catalyst was used to generate synthetically challenging polycyclic scaffolds through a one-pot cascade sequence. By controlling the ligand and reaction conditions, both 6,6,5-tricyclic and 6,6,6,5-tetracyclic cores were selectively synthesized in one operation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Yuwen Wang, Patrick Czabala, Monika Raj
Summary: In this study, the authors report a one-pot multicomponent Furan-Thiol-Amine reaction inspired by enzymes, which can generate stable pyrrole heterocycles independent of diverse functionalities. The reaction has wide applicability, including selective and irreversible labeling of peptides, synthesis of macrocyclic and stapled peptides, selective modification of different proteins with varying payloads, and labeling of lysine and cysteine in a complex human proteome.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Sachie Yamamoto, Zong Yang Zhou, Goki Hiruta, Katsuhiko Takeuchi, Jun-Chul Choi, Takeshi Yasuda, Takaki Kanbara, Junpei Kuwabara
Summary: The Povarov reaction is an efficient tool for the synthesis of aza-polycyclic aromatic hydrocarbons, with site selectivity depending on the HOMO distribution of the intermediate. Specific molecular structures can be synthesized through the Povarov reaction, with one derivative showing good performance as a hole-blocking material in organic light-emitting diodes.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mohammad Taghi Nazeri, Ali Beygzade Nowee, Ahmad Shaabani
Summary: An efficient one-pot reaction for the synthesis of a new class of pseudopeptides connected to sulfonamide via a tandem N-sulfonylation/Ugi four-component reaction strategy is reported in this study. The reaction is carried out using readily available starting materials in ethanol/water at room temperature. The synthesized compounds have the potential for designing modern drugs with highly desirable features.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Jian-Xiang Zhu, Fu Pi, Teng Sun, Wen-Yu Huang, Lu Gao, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: This article introduces a palladium-catalyzed tandem reaction that proceeds through sequential 2,4-dienylation/Michael addition/pi-sigma-pi isomerization/allylic alkylation. Using ortho-functionalized aryl enones and 2,4-dienyl carbonates as substrates, enantioenriched architectures with fused and spirocyclic frameworks are constructed in moderate to excellent yields and stereoselectivity. Importantly, the intrinsic intramolecular Diels-Alder reaction pattern of the dienylated intermediates is effectively reversed via Pd(0)-pi-Lewis base catalysis.
Article
Chemistry, Organic
Jonathan P. Knowles, Hannah G. Steeds, Maria Schwarz, Francesca Latter, Kevin Booker-Milburn
Summary: This method transforms simple starting materials into complex tetracyclic products with potential medicinal chemistry applications through a sophisticated chemical catalysis process.
Article
Chemistry, Organic
Bastian Altemeier, Harald Groeger
Summary: In this article, a new approach is described for applying thermodynamically unfavored reactions in synthetic chemistry and integrating them in cascade processes. By using a rotating reaction vessel and a multi-step one-pot synthesis procedure, a thermodynamically labile Diels-Alder adduct was successfully converted to the target product with high conversion and excellent yield. This combination of Diels-Alder reaction and hydrogenation enables efficient production of a valuable bio-based platform chemical and opens new possibilities for integrating thermodynamically unfavorable reactions in multi-step one-pot cascade processes to obtain high yields of desired target products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Ghanshyam Mali, Amar Nath Singh Chauhan, Kailas Arjun Chavan, Rohan D. Erande
Summary: The class of Double Diels-Alder (DDA) reactions leads to targets succinctly with conceptually novel and streamlined methods. This growing branch of Diels-Alder reactions triggers the streamlined construction of polycyclic and macrocyclic architectures. The emphasis is on the synthesis of various structural classes based on the selectivity of the DDA reaction.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jilai Wu, Song Xie, Xin Xu, Ziyi Zhou, Likai Zhou, Chao Wei, Xiaoliu Li, Chen Wu, Hua Chen
Summary: An efficient one-pot synthesis of structurally diverse tetrahydroquinoline-fused iminosugars through the aza-Diels-Alder mechanism has been developed. The method is adaptable for various imines and d/l-ribose tosylates, with both electron-donating and -withdrawing substituted imines showing good reaction efficiency.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Amar Nath Singh Chauhan, Ghanshyam Mali, Rohan D. Erande
Summary: The Diels-Alder reaction is a fascinating synthetic strategy known for its diverse targets and unique reaction mechanism. It has made extensive accomplishments in organic synthesis and holds significant importance in chemical science.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hongling Wang, Qiangqiang Zhang, Shuai Xiao, Guanjie Wang, Xuan Huang, Xingkuan Chen, Junmin Zhang
Summary: We have developed a N-heterocyclic carbene (NHC) and base-mediated [3 + 3] annulation reaction for the synthesis of enantioselective dihydropyrano[3,2-b]indoles. Easily prepared sulfonium salts were used as precursors and reacted with unsaturated acyl azolium to achieve this transformation. The reaction conditions are mild and result in privileged indole-fused dihydropyranones with moderate to good yields and excellent enantioselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Biochemistry & Molecular Biology
Hongliang Wei, Songmao Li, Zijun Liu, Hongli Chen, Yuhua Liu, Weikun Li, Gang Wang
Summary: Starch-cellulose interpenetrating network (IPN) hydrogels were prepared via sequential Diels-Alder click reaction and photopolymerization, with the addition of beta-cyclodextrin to improve performance. The sustained release behavior of drug-loaded hydrogels was studied using 5-fluorouracil as a model drug. The strategy shows potential for applications in preparing IPN hydrogels due to the controllable photopolymerization and catalyst-free Diels-Alder reaction.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2022)
Article
Chemistry, Multidisciplinary
Chengsen Cui, Mingji Dai
Summary: We present a highly efficient and convergent strategy for synthesizing UCS1025A and its diastereomer tetra-epi-UCS1025A. UCS1025A is a representative member of the naturally occurring pyrrolizidinone polyketides, some of which exhibit potent antibacterial, antifungal, and anticancer activities. Our approach involves a tandem carbonylative Stille cross coupling and Diels-Alder reaction to form a key C-C bond and construct the trans-decalin system. The process uses carbon monoxide as a linchpin to connect a vinyl triflate and a vinylstannane, resulting in the desired enone moiety for subsequent intramolecular Diels-Alder cyclization. Additionally, our synthesis provides a versatile method for synthesizing other pyrrolizidinone-containing polyketides.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Yi Li, Yicen Ge, Rui Sun, Xiao Yang, Shipeng Huang, Huajian Dong, Yunyao Liu, Haodan Xue, Xiaoyan Ma, Haiyan Fu, Zeqin Chen
Summary: A one-pot cascade reaction for the synthesis of 2,3-dihydropyridinones was achieved using 3-fluoro-2-iodo-1-methylpyridinium triflate as the halogen bond catalyst. The desired [4+2] cycloaddition products with aryl, heteroaryl, alkyl, and alicyclic substituents were obtained in yields of 28-99%. Mechanistic investigations confirmed the importance of the strong halogen-bonding interaction between the iodopyridinium catalyst and imine intermediate in masking the vulnerable C-I bond and accelerating the aza-Diels-Alder reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Konstantin F. Suzdalev, Julia V. Vyalyh, Valery V. Tkachev, Ekaterina A. Lysenko, Oleg N. Burov, Anton Lisovin, Mikhail E. Kletskii, Sergey Kurbatov
Summary: A new method for the annulation of a thiopyrane ring to an indole core under mild conditions has been developed. The reaction mechanism involves a stepwise addition through ion-pair formation, with the essential role of the Li atom at all stages of the process being revealed by AIM calculations.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Hari K. Kadam, Santosh G. Tilve
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Hari K. Kadam, Deesha D. Malik, Lalitprabha Salgaonkar, Ketan Mandrekar, Santosh G. Tilve
SYNTHETIC COMMUNICATIONS
(2017)
Review
Chemistry, Organic
Hari K. Kadam, Santosh G. Tilve
MINI-REVIEWS IN ORGANIC CHEMISTRY
(2019)
Correction
Chemistry, Organic
Hari K. Kadam, Deesha D. Malik, Lalitprabha Salgaonkar, Ketan Mandrekar, Santosh G. Tilve
SYNTHETIC COMMUNICATIONS
(2019)
Article
Chemistry, Organic
Hari K. Kadam, Santosh G. Tilve
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2013)
Editorial Material
Chemistry, Organic
Hari Krishna Kadam
Article
Chemistry, Organic
Hari K. Kadam, Salman Khan, Rupesh A. Kunkalkar, Santosh G. Tilve
TETRAHEDRON LETTERS
(2013)
Article
Chemistry, Organic
Ketan S. Mandrekar, Hari K. Kadam, Santosh G. Tilve
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Hari K. Kadam, Anushri Laxman Gawas, Shruti Sagun Vernekar, Anika Arjun Chodankar, Saurabh Sudan Gaonkar, Lalitprabha N. Salgaonkar, Tushar S. Anvekar, Teotone Vaz, Shashank N. Mhaldar
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Organic
Hari K. Kadam, Santosh G. Tilve
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
(2019)
Article
Chemistry, Organic
Hari K. Kadam, Santosh G. Tilve
Review
Chemistry, Organic
Hari K. Kadam, Santosh G. Tilve
Review
Chemistry, Multidisciplinary
Hari K. Kadam, Santosh G. Tilve
Article
Chemistry, Multidisciplinary
P. T. Parvatkar, H. K. Kadam, P. S. Parameswaran, S. G. Tilve
ASIAN JOURNAL OF CHEMISTRY
(2012)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
