Room-Temperature Electrophilic 5-endo-dig Chlorocyclization of Alk-3-yn-1-ones with the Use of Pool Sanitizer: Synthesis of 3-Chlorofurans and 5-Chlorofuropyrimidine Nucleosides
作者： Adam Sniady , Marco S. Morreale , Kraig A. Wheeler , Roman Dembinski
关键词:
摘要: The 5-endo-dig chlorocyclization of 1,4-disubstituted alk-3-yn-1-ones (propargylic ketones) with the use trichloro-s-triazinetrione (trichloroisocyanuric acid, TCCA; 0.4 equiv.) in toluene, at room temperature, absence base, provides 2,5-disubstituted 3-chlorofurans high yields (79–96 %). reaction can be accomplished by using commercially available swimming pool sanitizer. Selected 3-chlorofuran was validated as a substrate for Suzuki–Miyaura coupling. In similar manner, 5-alkynyl-2′-deoxyuridines produces 5-chlorofuropyrimidine nucleosides (76–83 %), which are analogues potent anitviral agents. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
sci-hub.se 参考文章(35)
Noor Esho, Brian Davies, Janet Lee, Roman Dembinski, Synthesis of dicobalt hexacarbonyl 5-p-tolylethynyl-2′-deoxyuridine Chemical Communications. pp. 332- 333 ,(2002) , 10.1039/B109501C
Adam Sniady, Audrey Durham, Marco S. Morreale, Andrzej Marcinek, Slawomir Szafert, Tadeusz Lis, Krystyna R. Brzezinska, Takanori Iwasaki, Takashi Ohshima, Kazushi Mashima, Roman Dembinski, Zinc-catalyzed cycloisomerizations. Synthesis of substituted furans and furopyrimidine nucleosides. Journal of Organic Chemistry. ,vol. 73, pp. 5881- 5889 ,(2008) , 10.1021/JO8007995
Adam F. Littke, Chaoyang Dai, Gregory C. Fu, Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions Journal of the American Chemical Society. ,vol. 122, pp. 4020- 4028 ,(2000) , 10.1021/JA0002058
Ulf Tilstam, Hilmar Weinmann, Trichloroisocyanuric Acid: A Safe and Efficient Oxidant Organic Process Research & Development. ,vol. 6, pp. 384- 393 ,(2002) , 10.1021/OP010103H
Anna Claudia Cunha, Fernanda Menezes da Paixão, Maria Cecília B. V. de Souza, Vitor Francisco Ferreira, CLORETO ISOCIANÚRICO E CLORETO CIANÚRICO: ASPECTOS GERAIS E APLICAÇÕES EM SÍNTESE ORGÂNICA Química Nova. ,vol. 29, pp. 520- 527 ,(2006) , 10.1590/S0100-40422006000300021
Diego Alves, Cristiane Luchese, Cristina W. Nogueira, Gilson Zeni, Electrophilic cyclization of (Z)-selenoenynes: synthesis and reactivity of 3-iodoselenophenes. Journal of Organic Chemistry. ,vol. 72, pp. 6726- 6734 ,(2007) , 10.1021/JO070835T
Alexei S. Karpov, Eugen Merkul, Thomas Oeser, Thomas J. J. Müller, One‐Pot Three‐Component Synthesis of 3‐Halofurans and 3‐Chloro‐4‐iodofurans European Journal of Organic Chemistry. ,vol. 2006, pp. 2991- 3000 ,(2006) , 10.1002/EJOC.200600225
Noor Esho, Jean-Paul Desaulniers, Brian Davies, Helen M.-P. Chui, Meneni Srinivasa Rao, Christine S. Chow, Slawomir Szafert, Roman Dembinski, NMR conformational analysis of p-tolyl furanopyrimidine 2′-deoxyribonucleoside and crystal structure of its 3′,5′-di-O-acetyl derivative Bioorganic & Medicinal Chemistry. ,vol. 13, pp. 1231- 1238 ,(2005) , 10.1016/J.BMC.2004.11.013
Timothy J. Donohoe, Lisa P. Fishlock, Adam R. Lacy, Panayiotis A. Procopiou, A metathesis-based approach to the synthesis of furans. Organic Letters. ,vol. 9, pp. 953- 956 ,(2007) , 10.1021/OL062933R
Hongwei Zhou, Jinzhong Yao, Guoliang Liu, Electrophilic cyclization of 4-thio-but-2-yn-1-ols via 1,2-migration of the thio group: efficient synthesis of 2,4-dihalo-3-thio-substituted furans Tetrahedron Letters. ,vol. 49, pp. 226- 228 ,(2008) , 10.1016/J.TETLET.2007.11.092