Indoloquinolines, Indolobenzoxazines and Quinazolophthalazines Prepared from Norbornane/eneamino Acids and Hydrazides

Abstract

Keywords: Indoloquinolines / Indolobenzoxazines / Quinazolophthalazines / NMR spectroscopy / DIFFNOE / X-ray diffractionThe reactions of di-endo-and di-exo-aminonorbornane/enecarboxylic acids 1-4 with ethyl 2-(2-oxocyclohexyl)acetate afforded methanoindoloquinolines 5, 6, 8, and 9, the oxo ester participating as a two-membered sp 2 building block. In the cases of di-exo-and di-endo-aminonorbornenecarboxylic acids 2 and 4, methanoindolobenzoxazinediones 7 and 10 were also formed; compound 7 was also isolated from the mother liquor of 10. The reactions of ethyl 2-(2-oxocy-

Bicyclic β-amino acids

“…The only exception is reaction of amino acids 31a/32a and 31b/32b or derivatives thereof with 1,4-dicarbonyl compounds like levullinic acid, leading to the (predominant) formation of products of the type 59 and 60, respectively. 49,50 The polycyclic compounds like those shown in Table 1 might remain just fanciful structures if their retro-Diels − Alder degradation was not discovered. The reaction was characteristic for the products derived from unsaturated amino acids 31/33, and virtually in all cases studied -from 31a,b (the exo isomers requiring milder conditions) (Scheme 16).…”