Novel ring transformations of pyrazines by intramolecular diels-alder reactions |
| |
| Institution: | 1. Laboratory of organic Chemistry, Agricultural University Wageningen, De Dreijen 5, 6703 BC Wageningen, The Netherlands;2. Department of Organic Chemistry, Medical Academy, Grunwaldzka 6, 60-780 Poznan, Poland;1. Department of Pharmaceutical Engineering, Hefei University of Technology, Hefei 230009, China;2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;1. Ufa Institute of Chemistry, Russian Academy of Sciences, 450054 Ufa, Russian Federation;2. Institute of Biochemistry and Genetics, Ufa Scientific Centre of the Russian Academy of Sciences, 450054 Ufa, Russian Federation;3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;1. Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetsky pr., 26, Saint-Petersburg, Petrodvorets 198504, Russia;2. Department of Chemistry, Saint Petersburg State Forest Technical University, Institutskyper., 5, Saint Petersburg 194021, Russia |
| |
| Abstract: | Pyrazines carrying the ω-alkyne side-chain -XCH2CH2C≡CH, (X = 0,N,S,SO,SO2, C(CN)2) undergo on heating an intramolecular Diels-Alder reaction. Pyrazines with the electron donating atom (0,N or S) in the side-chain afford c]-fused pyridines as main products, whereas (3-buty-nylsulfinyl)pyrazine and (3-butynylsulfonyl)pyrazine are exclusively converted into b]-fused pyridines. A b]-fused pyridine is also the major product in the reaction of 2,5-bis(1,1-dicyano-4-pentynyl)pyrazine. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
