The 1,3-dipolar cycloaddition of azomethine ylides generated in situ from the decarboxylative condensation of acenaphthenequinone and tyrosine or phenylalanine to β-nitrostyrenes afforded spiro acenaphthylene-pyrrolidine hybrids. The subsequent reaction of these spiro heterocycles with formaldehyde and trifluoroacetic acid led to the formation of either Pictet-Spengler or Eschweiler-Clarke products depending on the substitution in the benzyl ring. The unsubstituted compounds occurred via Pictet-Spengler route to afford spiro acenaphthylene pyrrolo[1,2-b]isoquinoline hybrids as expected, whereas the 4-OH substituted compounds proceeded via Eschweiler-Clarke route affording the unexpected N-methylated spiro acenaphthylene-pyrrolidine hybrids.

从啶醌和酪氨酸或苯丙氨酸的脱羧缩合到β-硝基苯乙烯的原位产生的偶氮甲碱的1，3-偶极环加成反应得到螺iro烯-吡咯烷杂化物。这些螺环杂环与甲醛和三氟乙酸的后续反应导致形成Pictet-Spengler或Eschweiler-Clarke产物，具体取决于苄环上的取代。未取代的化合物通过Pictet-Spengler途径出现，提供了预期的螺并吡咯并[1,2- b ]异喹啉杂化物，而4-OH取代的化合物通过Eschweiler-Clarke途径进行了处理，从而提供了出乎意料的N-甲基化的螺iro并吡咯烷-吡咯烷杂化物。