PYRROLES FROM AZAINDOLES . A SYNTHESIS OF PORPHOBILINOGEN AND RELATED PYRROLES
PYRROLES FROM AZAINDOLES . A SYNTHESIS OF PORPHOBILINOGEN AND RELATED PYRROLES
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DOI：
10.1021/ja01037a025
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发表时间：
1969-01-01
影响因子：
15
通讯作者：
RAPOPORT, H
中科院分区：
文献类型：
--
作者：
FRYDMAN, B;REIL, S;RAPOPORT, H
报道了一种合成2-氨甲基-3-吡咯乙酸的新方法。2-甲氧基-4-甲基-5-硝基吡啶和2-苄氧基-4-甲基-5-硝基吡啶与草酸二乙酯缩合，得到相应的邻硝基吡啶丙酮酸乙酯，经加氢转化为取代的6-氮杂吲哚-2-羧酸乙酯。吡咯并吡啶酮经醚裂解和氢化得到相应的羧基吡咯内酰胺，后者经脱羧和水解得到2-氨甲基-3-吡咯乙酸。用丙酸和乙酸侧链取代6-氮杂吲哚的C-3位，重复上述顺序，得到胆色素原和2-氨甲基-3，4-吡咯二乙酸。
A new method for the synthesis of 2-aminomethyl-3-pyrroleacetic acids is described. The condensation of 2-methoxy-and 2-benzyloxy-4-methyl-5-nitropyridine with diethyl oxalate afforded the corresponding ethyl o-nitropyridinepyruvates, which on hydrogenation were transformed into the substituted ethyl 6-azaindole-2-carboxylates. Cleavage of the ethers and hydrogenation of the resultingpyrrolopyridones yieldedthe corresponding carboxypyrrole lactams which on decarboxylation and hydrolysis gave the 2-aminomethyl-3-pyrroleacetic acids. Substitution at the C-3 position of the 6-azaindole with a propionic acid and acetic acid side chain and repetition of the above sequence gave porphobilinogen and 2-aminomethyl-3, 4-pyrrolediacetic acid.