Preparation and novel reduction reactions of vinamidinium salts
Preparation and novel reduction reactions of vinamidinium salts
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DOI：
10.1021/jo005656p
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发表时间：
2001-01-12
影响因子：
3.6
通讯作者：
Reider, PJ
中科院分区：
文献类型：
--
作者：
Davies, IW;Taylor, M;Reider, PJ
取代的乙酸和甲酰胺在三氯氧磷存在下反应，以中等至良好的未优化重结晶产率（40-67%）产生作为容易处理的非吸湿性固体的六氟磷酸乙烯脒鎓盐5a-d、6a-d和7。通过胺交换以81%产率制备1，3-差异取代的vinamidinium盐8，环状二氮杂卓盐9和10以> 76%产率制备。对称的2-氯vinamidinium 11通过3的置换以71%的产率制备。使用HI或PPh 3/pTSA以高达99%的测定产率将2-氯vinamidinium盐干净地还原为母体vinamidinium盐12-16。
Substituted acetic acids and formamides react in the presence of phosphorus oxychloride to yield the vinamidinium hexafluorophosphate salts 5a-d, 6a-d, and 7 in moderate to good unoptimized recrystallized yields (40-67%) as easily handled nonhygroscopic solids. The 1,3-differentially substituted vinamidinium salts 8 was prepared by amine exchange in 81% yield as are the cyclic diazapinium salts 9 and 10 in > 76% yield. The symmetrical 2-chlorovinamidinium 11 was prepared by displacement of 3 in 71% yield. The 2-chlorovinamidinium salts are cleanly reduced to the parent vinamidinium salts 12-16 using HI or PPh3/pTSA in up to 99% assay yield.