Journal ArticleDOI
Recent advances in isoxazole chemistry
Alexey V. Galenko,Alexander F. Khlebnikov,Mikhail S. Novikov,V. V. Pakal’nis,Nikolai V. Rostovskii +4 more
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TLDR
In this paper, the preparation methods and reactions of isoxazoles are described and systematized on the basis of analysis of the literature published from 2005 to present, and major attention is focused on the most efficient approaches: condensation of hydroxylamine with 1,3-dielectrophiles and reactions with nitrile oxides with alkenes and alkynes.Abstract:
The preparation methods and reactions of isoxazoles are described and systematized on the basis of analysis of the literature published from 2005 to present. In the discussion of synthesis, major attention is focused on the most efficient approaches: condensation of hydroxylamine with 1,3-dielectrophiles and reactions of nitrile oxides with alkenes and alkynes. Five-membered ring opening reactions leading to acyclic functionalized or other heterocyclic compounds are considered. The transformations of isoxazole derivatives that occur without ring cleavage to form fused heterocyclic systems, as well as reactions that lead to the introduction of C-substituents into isoxazoles, are considered. Data on the biological activity of some isoxazole derivatives are reported. The bibliography includes 439 references.read more
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Development of Gold-catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles.
TL;DR: Two new gold-catalyzed annulations of isoxazoles with propiolates with Propiolates have been developed, arising initially from two seven-membered heterocyclic intermediates, which then lead to products.
Journal ArticleDOI
Modern Trends of Organic Chemistry in Russian Universities
A. I. Konovalov,A. I. Konovalov,Igor S. Antipin,Igor S. Antipin,Vladimir Burilov,Timur I. Madzhidov,Almira Kurbangalieva,A. V. Nemtarev,A. V. Nemtarev,Svetlana E. Solovieva,Svetlana E. Solovieva,Ivan I. Stoikov,Vakhid A. Mamedov,L. Ya. Zakharova,Elena L. Gavrilova,Oleg G. Sinyashin,Irina A. Balova,Aleksander V. Vasilyev,Igor G. Zenkevich,M. Yu. Krasavin,Mikhail A. Kuznetsov,Alexander P. Molchanov,M. S. Novikov,Valerij A. Nikolaev,Ludmila L. Rodina,Alexander F. Khlebnikov,Irina P. Beletskaya,Sergey Z. Vatsadze,Sergey P. Gromov,Nikolai V. Zyk,Albert T. Lebedev,Dmitrii A. Lemenovskii,Valery S. Petrosyan,V. G. Nenaidenko,Vad. V. Negrebetskii,Yu. I. Baukov,T. A. Shmigol,Alexander A. Korlyukov,Alexander S. Tikhomirov,Andrey E. Shchekotikhin,Valerii F. Traven,L. G. Voskresenskii,Fedor I. Zubkov,O. A. Golubchikov,Alexander S. Semeikin,D. B. Berezin,Pavel A. Stuzhin,Victor D. Filimonov,Elena A. Krasnokutskaya,A. Yu. Fedorov,Alexander V. Nyuchev,V. Yu. Orlov,R. S. Begunov,A. I. Rusakov,A. V. Kolobov,E. R. Kofanov,O. V. Fedotova,A. Yu. Egorova,Valery N. Charushin,Oleg N. Chupakhin,Yu. N. Klimochkin,Vitaly A. Osyanin,Alexander N. Reznikov,A. S. Fisyuk,A. S. Fisyuk,G. P. Sagitullina,Alexander V. Aksenov,Nicolai A. Aksenov,M. K. Grachev,V. I. Maslennikova,Mikhail P. Koroteev,A. K. Brel,S. V. Lisina,S. M. Medvedeva,Kh. S. Shikhaliev,G. A. Suboch,Mikhail S. Tovbis,L. M. Mironovich,Sergey M. Ivanov,Sergey M. Ivanov,S. V. Kurbatov,M. E. Kletskii,O. N. Burov,K. I. Kobrakov,D. N. Kuznetsov +84 more
TL;DR: In this paper, a review devoted to the scientific achievements of the departments of organic chemistry in higher schools of Russia within the past decade is presented, focusing on the recent years of the 1990s.
Journal ArticleDOI
Metal-catalyzed 1,3-dipolar cycloaddition reactions of nitrile oxides
Silvia Roscales,Joaquín Plumet +1 more
TL;DR: Advances in the metal-catalyzed 1,3-dipolar cycloaddition reactions of nitrile oxides, mainly in the last decade, will be presented and discussed.
Journal ArticleDOI
Switchable Synthesis of Pyrroles and Pyrazines via Rh(II)-Catalyzed Reaction of 1,2,3-Triazoles with Isoxazoles: Experimental and DFT Evidence for the 1,4-Diazahexatriene Intermediate.
Nikolai V. Rostovskii,Julia O. Ruvinskaya,Mikhail S. Novikov,Alexander F. Khlebnikov,Ilia A. Smetanin,Anastasiya V. Agafonova +5 more
TL;DR: 4-Aminopyrrole-3-carboxylates and pyrazine-2-car boxylates were synthesized from 5-alkoxyisoxazoles and 1-sulfonyl-1,2,3-triazoles by tuning the Rh(II) catalyst and the reaction conditions.
References
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Journal ArticleDOI
Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.
Fahmi Himo,Timothy Lovell,Robert Hilgraf,Vsevolod V. Rostovtsev,Louis Noodleman,K. Barry Sharpless,Valery V. Fokin +6 more
TL;DR: Huisgen's 1,3-dipolar cycloadditions become nonconcerted when copper(I) acetylides react with azides and nitrile oxides, providing ready access to 1,4-disubstituted 1,2, 3-triazoles and 3, 4-disubsided isoxazoles, respectively.
Journal ArticleDOI
The Reactions of Primary Nitroparaffins with Isocyanates1
Teruaki Mukaiyama,Toshio Hoshino +1 more
Journal ArticleDOI
Carboxylation of C-H bonds using N-heterocyclic carbene gold(I) complexes.
TL;DR: A highly efficient [(NHC)Au(I)]-based (NHC = N-heterocyclic carbene) catalytic system for the carboxylation of aromatic and heteroaromatic C-H bonds was developed and permits the facile functionalization of C- H bonds without the use of other organometallic reagents.
Journal ArticleDOI
Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides.
TL;DR: Palladium-catalyzed C-H activation: cheap aryl chlorides can now be used for the arylation of a wide variety of electron-rich heterocycles, and the key to the success is the use of a bulky, electron- rich phosphine ligand.
Journal ArticleDOI
Pd‐PEPPSI‐IPent: An Active, Sterically Demanding Cross‐Coupling Catalyst and Its Application in the Synthesis of Tetra‐Ortho‐Substituted Biaryls
TL;DR: A variety of sterically encumbered tetra-ortho-substituted biaryl products were formed from unreactive aryl chlorides using the isopentyl-subStituted catalyst at temperatures ranging from 65 degrees C to room temperature, demonstrating that "flexible bulk" is essential to promote these transformations.
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