Article
Chemistry, Organic
Vasyl Y. Hys, Demyd S. Milokhov, Tetiana Ye Keda, Iryna Omelchenko, Irina S. Konovalova, Svitlana Shishkina, Yulian M. Volovenko
Summary: An efficient synthesis method for novel 7-membered azacycles bearing heterofused amidine framework has been developed. The method utilizes ambiphilic building blocks in a base-mediated reaction sequence and demonstrates the synthetic utility of the obtained compounds. This method not only enables basic reactions such as hydrolysis and reduction, but also allows for the synthesis of complex nitrogen-containing heterocycles through cascade reactions.
Article
Chemistry, Organic
Vasyl Y. Hys, Maryna V. Babii, Demyd S. Milokhov, Alexey V. Dobrydnev, Yulian M. Volovenko
Summary: We present a developed method for the two-step synthesis of heterofused s-sultams, based on the alkylation of N-monosubstituted methanesulfonamides and the sulfa-Dieckmann condensation. The method has a broad substrate scope, and the target compounds show great synthetic potential.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Wai Fung Cheng, Shiqiang Ma, Yin Tung Lai, Yuen Tsz Cheung, Kornkamon Akkarasereenon, Yiqin Zhou, Rongbiao Tong
Summary: An intramolecular aza-Prins cyclization of aza-Achmatowicz rearrangement products was developed using bismuth tribromide as both an efficient Lewis acid and a bromide nucleophile source. This approach enables the construction of highly functionalized 9-azabicyclo[3.3.1]nonanes, which are valuable building blocks for alkaloid natural products and drug molecules. The application of this method to the total synthesis of six indole alkaloids demonstrates its significant synthetic utility.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Mina Rajabi, Jaydee Cabral, Sarah Saunderson, M. Azam Ali
Summary: Chitooligosaccharide (COS), an emerging material carbohydrate polymer, was prepared using a microwave-assisted process. The COS was then used to synthesize COS-poly(ethylene glycol) diacrylate (PEGDA) derivatives through aza-Michael addition. The resulting COS-PEGDA hydrogels showed high biocompatibility and can be potentially used in biomedical applications.
CARBOHYDRATE POLYMERS
(2022)
Article
Chemistry, Organic
Suraj, K. C. Kumara Swamy
Summary: Functionalized azetidines, 2,3-dihydrofurans, or the unorthodox dioxa-3-azabicyclonone-4-ene motifs can be synthesized through transition metal-free reactions. The reaction products depend on the reaction conditions used. The study also reveals the structure of the intermediate involved in the reaction. Additionally, isomeric diazocanes with separation and crystallization properties were successfully synthesized.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Na Li, Qian Wang, Shuping Zhuo, Li-Ping Xu
Summary: The mechanism, reactivity, and selectivity of the aza-Prins reaction were studied using theoretical calculations, both in bulk solution and under [Ga4L6](12-) supramolecular catalysis. In bulk solution, the steric effect and donor-acceptor interaction favor the parallel-conformation transition state, leading to the observed chemoselectivity that produces the alcohol product. However, under [Ga4L6](12-) catalysis, the host-guest noncovalent interaction and confinement effect play a more critical role, leading to the vertical-conformation transition state and switch in chemoselectivity that produces the piperidine product. These computational findings are consistent with experimental results and provide insights into the development of more efficient and selective supramolecular catalysis.
Article
Chemistry, Organic
Victoria Sinka, Daniel A. Cruz, Victor S. Martin, Juan I. Padron
Summary: The shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin were achieved using a common parallel synthetic strategy based on Prins-Peterson cyclization in their core construction. In only one step, a seven-membered ring oxacycle with the correct cis-stereochemistry ring closure and the Δ4 position of the endocyclic double bond in (+)-isolaurepinnacin was obtained. This unsaturation was also necessary to access the bromodioxabicycle in (+)-neoisoprelaurefucin.
Article
Chemistry, Organic
Roman Ivanov, Elizaveta Ivanova, Vladislav Merkulov, Mikhail Zharkov, Ilya Kuchurov, Sergei Zlotin
Summary: For the first time, amines have been condensed with carbonyl compounds in supercritical carbon dioxide (sc-CO2). The reactions with aldehydes or active ketones proceed at moderate temperatures without external catalysts. The process is autocatalytic, accelerated by the carbonic acid generated in situ. The imine products obtained in high yields in a crystalline form can be used in one-pot transfer hydrogenation and [4+2] cycloaddition reactions for green synthesis of more complex and valuable compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Xiao Hu, Minglin Tao, Zhongxiao Ma, Yi Zhang, Yanni Li, Deqiang Liang
Summary: A novel reaction method is proposed in this study, which enables regioselective tandem enamido beta-C(sp(2))-H alkylation/acrylamido alkylation/cyclizative alkenylation sequence of 3-aza-1,5-dienes under visible light irradiation. This method shows excellent regiospecificity and broad substrate scope.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Laura F. Pena, Enol Lopez, Angel Sanchez-Gonzalez, Asuncion Barbero
Summary: A convenient method has been developed for the regioselective synthesis of allyl- and vinylsilyl alcohols from a common precursor by selecting suitable reaction conditions. These alcohols have been used in silyl-Prins cyclizations to prepare disubstituted oxygenated heterocycles in a one-pot sequential reaction. The reaction outcomes are highly dependent on the starting alkenylsilyl alcohol and reaction conditions, with various competitive pathways observed. However, the use of vinylsilyl alcohols has shown promising results in the preparation of differentially substituted cis-2,6-dihydropyrans.
Article
Chemistry, Organic
Sho Amemiya, Shingo Okemoto, Akira Tsubouchi, Akio Saito
Summary: A synthetic method for alpha-(aminoethyl)-alpha,beta-enones from aryl-substituted homopropargyl sulfonamides and aldehydes was developed, representing the first synthesis of conjugated enones via alkyne aza-Prins cyclization. These products could be further converted into pyrrolidines.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Efraim Reyes, Liher Prieto, Uxue Uria, Luisa Carrillo, Jose L. Vicario
Summary: The Prins reaction is a convenient method for synthesizing oxygen-containing heterocyclic compounds, especially tetrahydropyrans and tetrahydrofurans. Recent years have seen impressive improvements in its performance and scope, particularly in the development of new catalytic and enantioselective versions.
Article
Chemistry, Organic
Robert E. Wiley, Michael F. McLaughlin, Jeffrey S. Johnson
Summary: Novel tetrahydroquinoline-containing spirocycles have been successfully synthesized through an acid-promoted dearomatization reaction, allowing for further elaboration of their chemical structures.
Article
Chemistry, Organic
Vitalii V. Izhyk, Anton O. Poliudov, Alexey V. Dobrydnev, Taras V. Omelian, Maria V. Popova, Yulian M. Volovenko
Summary: In this study, we present a short and cost-effective synthesis approach for alkyl isothiazolidine-1,1-dioxide 3-carboxylates starting from commercially available α-amino acid ester hydrochlorides. These compounds were designed as sulfonamide-containing bioisosteres of the known pharmacological template - pyroglutamic acid (pGlu).
Article
Chemistry, Organic
Jonathan Trevorrow, Anne O'Kearney-McMullan, Lucie Miller Potucka, Adrian P. Dobbs
Summary: In this study, we report a novel and highly efficient method for the synthesis of hydroxydi- and hydroxytetra-hydropyrans as spiroketal precursors. This method bypasses the challenges associated with traditional multistep syntheses and protecting group manipulation, providing a new pathway for studying the spiroketal moiety.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
