Article
Chemistry, Multidisciplinary
Pau Nadal Rodriguez, Ouldouz Ghashghaei, Anna M. M. Schoepf, Sam Benson, Marc Vendrell, Rodolfo Lavilla
Summary: Charting the chemical reaction space around the combination of carbonyls, amines, and isocyanoacetates allows the discovery of new multicomponent processes leading to a variety of unsaturated imidazolone scaffolds. The resulting compounds exhibit the chromophore of the green fluorescent protein and the core of the natural product coelenterazine. Despite the competitive nature of the pathways involved, general protocols provide selective access to desired chemotypes. Furthermore, unprecedented reactivity at the C-2 position of the imidazolone core is described, directly affording C, S, and N-derivatives featuring natural products (e.g. leucettamines), potent kinase inhibitors, and fluorescent probes with suitable optical and biological profiles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Daniel S. Verdoorn, Prabhat Ranjan, Tim de Reuver, Elwin Janssen, Christophe M. L. Vande Velde, Jordy M. Saya, Bert U. W. Maes, Romano V. A. Orru
Summary: A cobalt-(II) mediated three-component synthesis of 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2-(3H)-imines using sulfonyl azides, N-isocyanimino-triphenyl-phosphorane(NIITP), and carboxylic acids has been developed. The reaction proceeds through a nitrene transfer to NIITP, followed by addition of the carboxylic acid to the in situ formed carbodiimide and subsequent intramolecular aza-Wittig reaction. The selectivity towards the two products is determined by the steric constraints of carboxylic acid and the stoichiometry of the employed cobalt salt.
Article
Chemistry, Organic
Alexandre Quelhas, Houda Gazzeh, Thierry Roisnel, Yann Trolez, Jean-Claude Guillemin
Summary: Kinetically unstable vinyl, allenyl and propargyl isocyanides react faster in Passerini and Ugi reactions than they decompose, leading to functionalized amides that can be further used in reactions involving unsaturated substituents.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Li Gao, Shabnam Shaabani, Atilio Reyes Romero, Ruixue Xu, Maryam Ahmadianmoghaddam, Alexander Doemling
Summary: We demonstrate the feasibility of synthesizing a large library based on 16 different chemistries in parallel on a nanoscale using highly automated methods. Unlike combinatorial chemistry, we generate 16 scaffolds simultaneously, with each compound produced through a random combination of diverse building blocks in a sparse matrix fashion. The advantages of this automated nanoscale synthesis approach include library diversity, absence of storage logistics, superior economics, faster synthesis through automation, increased safety, and sustainable chemistry.
Article
Chemistry, Multidisciplinary
Scott Rice, Daniel J. Cox, Stephen P. Marsden, Adam Nelson
Summary: Regioselective and stereospecific directed C-H arylation of simple amine substrates, followed by cyclisation, resulted in the synthesis of 30 diverse, three-dimensional scaffolds. This unified approach significantly expanded the range of bridged ring systems containing both a nitrogen atom and an aromatic ring.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Applied
Chih-Yu Wu, Sivan Perumal Murugan, Yu-Wei Wang, Hao-Wei Pan, Bing-Jian Sun, Yu-Ting Lin, Siti Fatimah, Agnes H. H. Chang, Chinpiao Chen, Gene-Hsian Lee
Summary: This study developed an efficient method for preparing diastereo- and regio-selective indoline-fused 2,5-diketopiperazine scaffolds using Ugi reaction and a post-Ugi tandem reaction under basic conditions. The possible reaction mechanism and substrate structures were elucidated through single-crystal X-ray diffraction analysis and density functional theory calculations.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Zhiwei Chen, Piaopiao Zeng, Shuo Zhang, Xiaoxiao Huang
Summary: A concise one-pot route for the synthesis of furo[3,2-c]-coumarins catalyzed by Zn(OTf)(2) has been reported, allowing for the easy generation of libraries of furocoumarin analogues through multicomponent tandem reactions. This transformation is highly atom economical and exhibits good functional group compatibility.
Article
Genetics & Heredity
Giwon Shin, Stephanie U. Greer, Erik Hopmans, Susan M. Grimes, Hojoon Lee, Lan Zhao, Laura Miotke, Carlos Suarez, Alison F. Almeda, Sigurdis Haraldsdottir, Hanlee P. Ji
Summary: The study revealed the coexistence of different genomic instability states in colorectal carcinomas, with potential contribution from MSH3 mutation. Increased copy number of chromosome arm 8q was most prevalent in tumors with microsatellite instability, and subclonal analysis identified co-occurring driver mutations previously known to be exclusive.
Article
Chemistry, Multidisciplinary
Sivagami Mathavan, Rajesh B. R. D. Yamajala
Summary: A strategy for synthesizing a series of diverse 4H-pyrimido[2,1-b]benzothiazoles has been developed using elemental sulfur under metal and solvent-free conditions. This method allows for the easy synthesis of desired products in good to excellent yields, with broad substrate scope, inexpensive catalyst, and mild reaction conditions.
Article
Chemistry, Organic
Li Huang, Ying Han, Jing Sun, Qiu Sun, Chao-Guo Yan
Summary: The base promoted tandem annulation reaction of activated cyclic 1,3-dipolarophiles with functionalized furo[2,3-d]pyrimidine-2,4-diones provided efficient synthetic protocols for complex dispiro/dispiro fused tricyclic compounds. This reaction proceeded via sequential ring-opening, formal [3 + 2] cycloaddition, and annulation processes.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Chetan K. Jadhav, Amol S. Nipate, Asha Chate, Makrand Kulkarni, Vidya S. Dofe, Charansingh H. Gill
Summary: An efficient one-pot multicomponent synthesis of 3-amino-1-alkylpyridin-2(1H)-ones using 1,8-diazabicyclo [5,4,0] undec-7-enium acetate [DBUH][OAc] ionic liquid as a green solvent medium was achieved with mild conditions and outstanding conversion rates. The recyclability and recovery of the ionic liquid make this protocol environmentally desirable, and the synthesized compounds showed promising in vitro antitumor activity against human cancer cell lines.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Review
Multidisciplinary Sciences
Arvind Singh, Bhupinder Kaur, Aditi Sharma, Anu Priya, Manmeet Kaur, Mussarat Shamim, Bubun Banerjee
Summary: The present review provides a summary of the multi-component reaction strategies used in the synthesis of diverse bioactive heterocyclic scaffolds involving 6-aminouracil or its N-methyl derivatives over the last two decades.
PHYSICAL SCIENCES REVIEWS
(2022)
