SINGLET OXYGEN MEDIATED OXIDATIVE DECARBOXYLATION OF PYRROLE-2-CARBOXYLIC ACIDS
SINGLET OXYGEN MEDIATED OXIDATIVE DECARBOXYLATION OF PYRROLE-2-CARBOXYLIC ACIDS
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DOI：
10.1021/jo00024a045
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发表时间：
1991-11-22
影响因子：
3.6
通讯作者：
BALDINO, CM
中科院分区：
文献类型：
--
作者：
BOGER, DL;BALDINO, CM
1 5(35%)，6(32%)1 5(37%)，6(2 6%)1 5(79%)1 5(83%)1 5(6 2%)1 10(92%)1 10(80%)z浸泡井，Hanovia High-0，铀黄玻璃过滤器5高温反应容器，金红花钨，4我们研究了小分子氧(102)与取代的5-(烷氧羰基)吡咯-2-羧酸的加成反应和随后的氧化脱羧化反应，努力提供对方案I中发现的5-(烷氧羰基)-5-羟基-3-吡咯啉-2-酮亚基的直接访问。研究中使用的底物来自2-[(三乙基硅氧基)氧基]-2-丁烯和1，1-二甲氧基乙烯与3，6-二(甲氧基甲氧基)-1，2，4，5-四嗪7 8的[4+2]环加成反应，然后是生成的1，2，4，5-四氮杂环缩合(锌，HoAc)。2-二氮杂环加合物，以提供取代的吡咯2和7。吡咯的N-甲基化，然后是对称的吡咯3的令人惊讶的选择性单水解，以及众所周知的立体选择性水解。
1 5 (35%), 6 (32%) 1 5 (37%), 6 (26%) 1 5 (79%) 1 5 (83%) 1 5 (62%) 1 10 (92%) 1 10 (80%) z immersion well, Hanovia high-0, uranium yellow glass filter 5 Pyrex reaction vessel, tungsten chrysohermidin, 4 we have examined thesinglet oxygen (102) addition5 to substituted 5-(alkoxycarbonyl) pyrrole-2-carboxylic acids and a subsequent oxidative decarboxylation6 reaction in efforts to provide direct access to the 5-(alkoxycarbonyl)-5-hydroxy-3-pyrrolin-2-one subunit found in 1, Scheme I.The substrates employed in the study were derived from the [4+ 2] cycloaddition of 2-[(triethylsilyl) oxy]-2-butene and 1, 1-dimethoxyethylene with 3, 6-bis (methoxycarbonyl)-1, 2, 4, 5-tetrazine7 8followed by reductive ring contraction (Zn, HOAc) of the resulting 1, 2-diazinecy-cloadducts to provide the substituted pyrroles 2 and 7.® N-Methylation of the pyrroles followed by a surprisingly selective monohydrolysis of the symmetrical pyrrole 3 and a well-precedented9 selective hydrolysis of the sterically