期刊
MOLECULAR DIVERSITY
卷 21, 期 2, 页码 257-263出版社
SPRINGER
DOI: 10.1007/s11030-016-9721-8
关键词
Fused pyrrolizines; Spiro[acenaphthylenepyrrole]; 1, 3-Dipolar cycloaddition azomethine ylides; Acetylenic ester
An efficient synthesis of tetraalkyl 6a-hydroxy-3-alkyl-3H, 6aH-acenaphtho[1,2-g] pyrrolizine-1,2,5,6-tetra-carboxylates via the 1,3-dipolar cycloaddition reaction of azomethine ylides (generated in situ from alpha-amino acids and acenaphthylene-1,2-dione) with dialkyl acetylenedicarboxylates is described. When glycine was used instead of alanine, phenylalanine, valine, or isoleucine, dialkyl (E)-1'-(1,4-dialkoxy-1,4-dioxobut-2-en-2-yl)-2-oxo-1',5'-dihydro-2H-spiro [acenaphthylene-1,2'-pyrrole]-3',4'-dicarboxylates were obtained. The steric effects of the alpha-amino acids side chains may be responsible for their different behaviors.
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