Serafini-Cessi F, Cessi C
Biochem J. 1970 Dec;120(4):873-6. doi: 10.1042/bj1200873.
1-C-(1-Acetylacetonyl)-2-deoxy-2-(1-methyl-3-oxobut-1-enyl)amino -d-galactitol is obtained from the condensation of 2-amino-2-deoxy-d-galactose with pentane-2,4-dione in anhydrous solvent. On treatment with hot alkali it gives 2-methylpyrrole with 37% yield. By acid hydrolysis under mild conditions the compound loses the N substituent and from the resulting unstable derivative 2-methylpyrrole is obtained (52% yield). It is concluded that derivatives of aminohexoses substituted at C-1 with a dioxopentyl chain are the precursors of 2-methylpyrrole in the Cessi & Serafini-Cessi (1963) modification of the Elson-Morgan reaction. As demonstrated previously, products of condensation of aminohexoses with pentane-2,4-dione at the amino group are not converted directly into 2-methylpyrrole, but this step provides protection of the amino group during condensation at C-1.
1-C-(1-乙酰丙酮基)-2-脱氧-2-(1-甲基-3-氧代丁-1-烯基)氨基 -D-半乳糖醇是由2-氨基-2-脱氧-D-半乳糖与戊烷-2,4-二酮在无水溶剂中缩合得到的。用热碱处理时，它以37%的产率生成2-甲基吡咯。在温和条件下进行酸水解时，该化合物失去N取代基，并从所得不稳定衍生物中获得2-甲基吡咯（产率52%）。得出的结论是，在Cessi & Serafini-Cessi（1963年）对Elson-Morgan反应的改进中，在C-1位被二氧戊基链取代的氨基己糖衍生物是2-甲基吡咯的前体。如前所示，氨基己糖与戊烷-2,4-二酮在氨基处的缩合产物不会直接转化为2-甲基吡咯，但这一步骤在C-1位缩合过程中为氨基提供了保护。
