Diels-Alder reactions of 1,2,4-triazines. Synthesis of thieno[2,3-c]pyridines and 3,4-dihydro-2H-thiopyrano[2,3-c]pyridines from 6-(alkynylthio)-1,2,4-triazines
Diels-Alder reactions of 1,2,4-triazines. Synthesis of thieno[2,3-c]pyridines and 3,4-dihydro-2H-thiopyrano[2,3-c]pyridines from 6-(alkynylthio)-1,2,4-triazines
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DOI：
10.1021/jo00282a006
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发表时间：
1989-10
影响因子：
3.6
通讯作者：
E. Taylor;J. Macor
中科院分区：
文献类型：
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作者：
E. Taylor;J. Macor
6-（炔硫基）-1，2，4-三嗪的分子内Diels-Alder反应生成2，3-二氢噻吩并[2，3-c]吡啶和3，4-二氢-2R-噻喃并[2，3-c]吡啶。以这种方式由相应的6-（炔基亚磺酰基）-1，2，4-三嗪合成的1-氧代-2，3-二氢噻吩并[2，3-c]吡啶容易通过乙酸酐诱导的Pumnierer反应芳构化为噻吩并[2，3-c]吡啶。
Intramolecular Diels-Alder reactions of 6-(alkynylthio)-1, 2, 4-triazines are shown to give 2, 3-dihydrothieno-[2, 3-c] pyridines and 3, 4-dihydro-2R-thiopyrano [2, 3-c] pyridines. l-Oxo-2, 3-dihydrothieno [2, 3-c] pyridines synthesized in this fashion from the corresponding 6-(alkynylsulfinyl)-l, 2, 4-triazines are readily aromatizedto thieno [2, 3-cjpyridines by an acetic anhydride induced Pumnierer reaction.