Collect. Czech. Chem. Commun.
1947, 12, 292-304
https://doi.org/10.1135/cccc19470292
Addition des composés nitrosés sur un système conjugué
O. Wichterle
Crossref Cited-by Linking
- Vu Van, Powell Jair N., Ford Russell L., Patel Pooja J., Driver Tom G.: Development and Mechanistic Study of an Iron-Catalyzed Intramolecular Nitroso Ene Reaction of Nitroarenes. ACS Catal. 2023, 13, 15175. <https://doi.org/10.1021/acscatal.3c04483>
- Jäger Christina, Gregori Bernhard J., Aho Juhana A. S., Hallamaa Marleen, Deska Jan: Peroxidase-induced C–N bond formation via nitroso ene and Diels–Alder reactions. Green Chem. 2023, 25, 3166. <https://doi.org/10.1039/D2GC04827B>
- Yu Lei, Li Wenhai, Tapdara Anyawan, Kyne Sara Helen, Harode Mandeep, Babaahmadi Rasool, Ariafard Alireza, Chan Philip Wai Hong: Chiral Gold Complex Catalyzed Cycloisomerization/Regio- and Enantioselective Nitroso-Diels–Alder Reaction of 1,6-Diyne Esters with Nitrosobenzenes. ACS Catal. 2022, 12, 7288. <https://doi.org/10.1021/acscatal.2c01680>
- Ghosh Prasanjit, Mondal Swati Lekha, Baidya Mahiuddin: Ascending of Cycloaddition Strategy for N–O Heterocycles. Synthesis 2022, 54, 1043. <https://doi.org/10.1055/a-1703-6448>
- Utecht Greta, Jasiński Marcin: 3,6-Dihydro-2H-1,2-oxazines (microreview). Chem Heterocycl Comp 2016, 52, 143. <https://doi.org/10.1007/s10593-016-1847-1>
- Brulíková Lucie, Harrison Aidan, Miller Marvin J, Hlaváč Jan: Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes. Beilstein J. Org. Chem. 2016, 12, 1949. <https://doi.org/10.3762/bjoc.12.184>
- Eberlin Ludovic, Carboni Bertrand, Whiting Andrew: Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds. J. Org. Chem. 2015, 80, 6574. <https://doi.org/10.1021/acs.joc.5b00593>
- Nakashima Erika, Yamamoto Hisashi: Continuous flow of nitroso Diels–Alder reaction. Chem. Commun. 2015, 51, 12309. <https://doi.org/10.1039/C5CC03458B>
- Galvani Gilles, Lett Robert, Kouklovsky Cyrille: Regio‐ and Stereochemical Studies on the Nitroso‐Diels–Alder Reaction with 1,2‐Disubstituted Dienes. Chemistry A European J 2013, 19, 15604. <https://doi.org/10.1002/chem.201302905>
- Bodnar Brian S., Miller Marvin J.: Hetero‐Diels‐Alder‐Reaktionen von Nitrosocarbonylverbindungen als nützliches Verfahren in der organischen Synthese. Angewandte Chemie 2011, 123, 5746. <https://doi.org/10.1002/ange.201005764>
- Bodnar Brian S., Miller Marvin J.: The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses. Angew Chem Int Ed 2011, 50, 5630. <https://doi.org/10.1002/anie.201005764>
- Baidya Mahiuddin, Yamamoto Hisashi: Metal Nitrite: A Powerful Oxidizing Reagent. J. Am. Chem. Soc. 2011, 133, 13880. <https://doi.org/10.1021/ja206736q>
- Chaiyaveij Duangduan, Cleary Leah, Batsanov Andrei S., Marder Todd B., Shea Kenneth J., Whiting Andrew: Copper(II)-Catalyzed Room Temperature Aerobic Oxidation of Hydroxamic Acids and Hydrazides to Acyl-Nitroso and Azo Intermediates, and Their Diels–Alder Trapping. Org. Lett. 2011, 13, 3442. <https://doi.org/10.1021/ol201188d>
- Li Hailing, Gori Didier, Kouklovsky Cyrille, Vincent Guillaume: New chiral amino acid-derived α-acyloxynitroso reagents for asymmetric nitroso Diels–Alder reactions. Tetrahedron: Asymmetry 2010, 21, 1507. <https://doi.org/10.1016/j.tetasy.2010.05.016>
- Bollans Lee, Bacsa John, O’Farrell Daniel A., Waterson Scott, Stachulski Andrew V.: Syntheses of structurally diverse amino acids, including δ-hydroxylysine, using the acyl nitroso Diels–Alder reaction. Tetrahedron Letters 2010, 51, 2160. <https://doi.org/10.1016/j.tetlet.2010.02.076>
- Anand Amit, Bhargava Gaurav, Kumar Vipan, Mahajan Mohinder P.: A regio and diastereoselective transformation of 3-dienyl-2-azetidinones to novel pyrroloxazine. Tetrahedron Letters 2010, 51, 2312. <https://doi.org/10.1016/j.tetlet.2010.02.127>
- Stephenson G. Richard, Balfe Andrew M., Hughes David L., Kelsey Richard D.: Decomplexation–nitroso Diels–Alder (NDA) approach to C,D-ring functionalisation for hippeastrine. Tetrahedron Letters 2010, 51, 6806. <https://doi.org/10.1016/j.tetlet.2010.09.118>
- Yang Baiyuan, Lin Weimin, Krchnak Viktor, Miller Marvin J.: Retro iminonitroso Diels–Alder reactions: interconversion of nitroso cycloadducts. Tetrahedron Letters 2009, 50, 5879. <https://doi.org/10.1016/j.tetlet.2009.07.121>
- Lin Weimin, Gupta Anuradha, Kim Kyung Hee, Mendel David, Miller Marvin J.: Syntheses of New Spirocarbocyclic Nucleoside Analogs Using Iminonitroso Diels−Alder Reactions. Org. Lett. 2009, 11, 449. <https://doi.org/10.1021/ol802553g>
- Bollans Lee, Bacsa John, Iggo Jonathan A., Morris Gareth A., Stachulski Andrew V.: The acyl nitroso Diels–Alder (ANDA) reaction of sorbate derivatives: an X-ray and 15N NMR study with an application to amino-acid synthesis. Org. Biomol. Chem. 2009, 7, 4531. <https://doi.org/10.1039/b912963d>
- Howard Judith A. K., Ilyashenko Gennadiy, Sparkes Hazel A., Whiting Andrew, Wright Allen R.: Mechanistic Insights into Transition Metal‐Catalysed Oxidation of a Hydroxamic Acid with in situ Diels–Alder Trapping of the Acyl Nitroso Derivative. Adv Synth Catal 2008, 350, 869. <https://doi.org/10.1002/adsc.200700568>
- Krchňák Viktor, Moellmann Ute, Dahse Hans-Martin, Miller Marvin J.: Solid-Supported Nitroso Hetero Diels–Alder Reactions. 2. Arylnitroso Dienophiles: Scope and Limitations. J. Comb. Chem. 2008, 10, 104. <https://doi.org/10.1021/cc7001414>
- Zhao Dongbo, Johansson Mikael, Bäckvall Jan‐E.: In Situ Generation of Nitroso Compounds from Catalytic Hydrogen Peroxide Oxidation of Primary Aromatic Amines and Their One‐Pot Use in Hetero‐Diels–Alder Reactions. Eur J Org Chem 2007, 2007, 4431. <https://doi.org/10.1002/ejoc.200700368>
- Templin Stephen S., Wallock Nathaniel J., Haworth Daniel T., Donaldson William A., Bennett Dennis W., Siddiquee Tasneem: Cycloaddition reactions of phthalimide substituted cyclic polyenes with heteroatom dienophiles. Journal of Heterocyclic Chem 2007, 44, 719. <https://doi.org/10.1002/jhet.5570440334>
- Howard Judith A. K., Ilyashenko Gennadiy, Sparkes Hazel A., Whiting Andrew: Development of new transition metal catalysts for the oxidation of a hydroxamic acid with in situ Diels–Alder trapping of the acyl nitroso derivative. Dalton Trans. 2007, 2108. <https://doi.org/10.1039/B704728B>
- Yamamoto Hisashi, Kawasaki Masanori: Nitroso and Azo Compounds in Modern Organic Synthesis: Late Blooming but Very Rich. Bulletin of the Chemical Society of Japan 2007, 80, 595. <https://doi.org/10.1246/bcsj.80.595>
- Yamamoto Yuhei, Yamamoto Hisashi: Recent Advances in Asymmetric Nitroso Diels–Alder Reactions. Eur J Org Chem 2006, 2006, 2031. <https://doi.org/10.1002/ejoc.200500847>
- Xu Ming, Vasella Andrea: A New Synthesis of Pteridines. Helvetica Chimica Acta 2006, 89, 1140. <https://doi.org/10.1002/hlca.200690111>
- Kalita Biswajit, Nicholas Kenneth M.: Copper-catalyzed allylic hydroxyamination and amination of alkenes with Boc-hydroxylamine. Tetrahedron Letters 2005, 46, 1451. <https://doi.org/10.1016/j.tetlet.2005.01.024>
- Yamamoto Hisashi, Momiyama Norie: Rich chemistry of nitroso compounds. Chem. Commun. 2005, 3514. <https://doi.org/10.1039/b503212c>
- Calvet Géraldine, Guillot Régis, Blanchard Nicolas, Kouklovsky Cyrille: Intermolecular nitroso Diels–Alder cycloaddition of α-acetoxynitroso derivatives in aqueous medium. Org. Biomol. Chem. 2005, 3, 4395. <https://doi.org/10.1039/b513397a>
- Miller Craig A., Batey Robert A.: Hetero Diels−Alder Reactions of Nitrosoamidines: An Efficient Method for the Synthesis of Functionalized Guanidines. Org. Lett. 2004, 6, 699. <https://doi.org/10.1021/ol0363117>
- Ragaini Fabio, Cenini Sergio, Brignoli Daniela, Gasperini Michela, Gallo Emma: Synthesis of Oxazines and N-Arylpyrroles by Reaction of Unfunctionalized Dienes with Nitroarenes and Carbon Monoxide, Catalyzed by Palladium−Phenanthroline Complexes. J. Org. Chem. 2003, 68, 460. <https://doi.org/10.1021/jo0260589>
- Flower Kevin R., Lightfoot Andrew P., Wan Hayley, Whiting Andrew: The development and application of ruthenium catalysed oxidations of a hydroxamic acid and in situ Diels–Alder trapping of the acyl nitroso derivative. J. Chem. Soc., Perkin Trans. 1 2002, 2058. <https://doi.org/10.1039/B206430H>
- G. Tsoungas Petros: Synthesis of 1,2-Oxazines and Their N-Oxides. HETEROCYCLES 2002, 57, 1149. <https://doi.org/10.3987/REV-02-547>
- Ragaini Fabio, Cenini Sergio, Borsani Elena, Dompé Mauro, Gallo Emma, Moret Massimo: Synthesis of N-Arylpyrroles, Hetero-Diels−Alder Adducts, and Allylic Amines by Reaction of Unfunctionalized Dienes with Nitroarenes and Carbon Monoxide, Catalyzed by Ru(CO)3(Ar-BIAN). Organometallics 2001, 20, 3390. <https://doi.org/10.1021/om010076j>
- Vogt Paul F., Miller Marvin J.: Development and applications of amino acid-derived chiral acylnitroso hetero Diels-Alder reactions. Tetrahedron 1998, 54, 1317. <https://doi.org/10.1016/S0040-4020(97)10072-2>
- Kresze Günter, Ascherl Bernhard, Braun Heinz, Felber Helena: α-HALONITROSO COMPOUNDS. A REVIEW. Organic Preparations and Procedures International 1987, 19, 329. <https://doi.org/10.1080/00304948709356201>
- Felber Helena, Kresze Günther, Prewo Roland, Vasella Andrea: Diastereoselectivity and Reactivity in the Diels‐Alder Reactions of α‐Chloronitroso Ethers. Helvetica Chimica Acta 1986, 69, 1137. <https://doi.org/10.1002/hlca.19860690522>
- Weinreb Steven M., Staib Ronald R.: Synthetic aspects of diels-alder cycloadditions with heterodienophiles. Tetrahedron 1982, 38, 3087. <https://doi.org/10.1016/0040-4020(82)80047-1>
- Kesler Ewa: Diels‐alder reaction of 2‐chloro‐2‐nitrosopropane with 1,3‐cyclohexadiene. Journal of Heterocyclic Chem 1980, 17, 1113. <https://doi.org/10.1002/jhet.5570170555>
- Klamann Dieter, Weyerstahl Peter, Fligge Manfred, Ulm Klaus: Zur Hydrierung des 1.2‐Oxazin‐Ringsystems. Chem. Ber. 1966, 99, 561. <https://doi.org/10.1002/cber.19660990228>
- Firl Joachim, Kresze Günter: Heterocyclen durch Diensynthese, III. Pyrrole, α‐Pyrone und Pyridone aus Diels‐Alder‐Addukten von Nitrosoverbindungen. Chem. Ber. 1966, 99, 3695. <https://doi.org/10.1002/cber.19660991137>
- Klamann Dieter, Weyerstahl Peter, Fligge Manfred, Kratzer Jakob: 3.6‐Dihydro‐2H‐1.2‐oxazine durch Diels‐Alder‐Synthesen mit Nitrosoverbindungen. Justus Liebigs Ann. Chem. 1965, 686, 122. <https://doi.org/10.1002/jlac.19656860116>
- Kresze G., Maschke A., Albrecht R., Bederke K., Patzschke H. P., Smalla H., Trede A.: Organic N‐Sulfinyl Compounds. Angew. Chem. Int. Ed. Engl. 1962, 1, 89. <https://doi.org/10.1002/anie.196200891>
- Arbuzov Yu. A., Fedyukina N. L., Shabyrina V. V., Shepeleva R. I.: The reactions of dienic hydrocarbons with nitroso compounds. Russ Chem Bull 1953, 1, 539. <https://doi.org/10.1007/BF01172011>