Diels–Alder reaction of fused pyran-2-ones with ethyl vinyl ether

作者: Amadej Juranovič , Krištof Kranjc , Slovenko Polanc , Franc Perdih , Marijan Kočevar

DOI: 10.1007/S00706-012-0734-4

关键词:

摘要: Ethyl vinyl ether was found to be an appropriate synthetic equivalent of acetylene for a set Diels–Alder reactions with fused pyran-2-ones that yield carbocyclic systems. Transformations were conducted under microwave irradiation DABCO (as catalyst the elimination ethanol) and n-butanol as additive. A single-crystal X-ray diffraction structure is presented N-(5,6,7,8-tetrahydro-6-methyl-8-oxonaphthalen-2-yl)benzamide.

参考文章(57)
Zbyszek Otwinowski, Wladek Minor, Processing of X-ray diffraction data collected in oscillation mode Methods in Enzymology. ,vol. 276, pp. 307- 326 ,(1997) , 10.1016/S0076-6879(97)76066-X
R Vijaya, T.C Dinadayalane, G Narahari Sastry, Diels–Alder reactions between cyclic five-membered dienes and acetylene Journal of Molecular Structure: THEOCHEM. ,vol. 589-590, pp. 291- 299 ,(2002) , 10.1016/S0166-1280(02)00284-1
Yuna Sato, Kouji Kuramochi, Takahiro Suzuki, Atsuo Nakazaki, Susumu Kobayashi, The second generation synthesis of (+)-pseudodeflectusin Tetrahedron Letters. ,vol. 52, pp. 626- 629 ,(2011) , 10.1016/J.TETLET.2010.11.153
Jure Hren, Franc Perdih, Slovenko Polanc, Marijan Kočevar, Retention of Symmetry Versus Desymmetrization for Bicyclo[2.2.2]octenes in the Presence of a Bridgehead Amide Group European Journal of Organic Chemistry. ,vol. 2011, pp. 3368- 3374 ,(2011) , 10.1002/EJOC.201100104
Nenad Maraš, Slovenko Polanc, Marijan Kočevar, Microwave-assisted methylation of phenols with tetramethylammonium chloride in the presence of K2CO3 or Cs2CO3 Tetrahedron. ,vol. 64, pp. 11618- 11624 ,(2008) , 10.1016/J.TET.2008.10.024
Christopher A. Hunter, Jeremy K. M. Sanders, The nature of .pi.-.pi. interactions Journal of the American Chemical Society. ,vol. 112, pp. 5525- 5534 ,(1990) , 10.1021/JA00170A016
Krištof Kranjc, Slovenko Polanc, Marijan Kočevar, Diels-Alder reactions of fused pyran-2-ones with maleimides: efficient syntheses of benz[e]isoindoles and related systems. Organic Letters. ,vol. 5, pp. 2833- 2836 ,(2003) , 10.1021/OL034852Q
Vita Majce, Marijan Kočevar, Slovenko Polanc, A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides Tetrahedron Letters. ,vol. 52, pp. 3287- 3290 ,(2011) , 10.1016/J.TETLET.2011.04.066
Kamyar Afarinkia, Victoria Vinader, Todd D. Nelson, Gary H. Posner, Diels-Alder cycloadditions of 2-pyrones and 2-pyridones Tetrahedron. ,vol. 48, pp. 9111- 9171 ,(1992) , 10.1016/S0040-4020(01)85607-6
Vivek Polshettiwar, Rajender S. Varma, Microwave-assisted organic synthesis and transformations using benign reaction media. Accounts of Chemical Research. ,vol. 41, pp. 629- 639 ,(2008) , 10.1021/AR700238S