✍ Scribed by Géza Stájer; Angela E. Szabó; Antal Csámpai; Pál Sohár
No coin nor oath required. For personal study only.
Whereas the cyclizations of di‐endo‐3‐aminobicyclo[2.2.1]heptane‐2‐carboxylic acid (2) and di‐endo‐3‐aminobicyclo[2.2.1]hept‐5‐ene‐2‐carboxylic acid (3) with 4‐oxopentanoic acid (1) yield methanodioxopyrrolo[1,2‐a][3,1]benzoxazines 6 and 7, the di‐exo analogues give either the pyrrolo[1,2‐a]pyridine 8 as sole product (in the case of 4), or 10 together with the methyl‐substituted derivative 9 (in the case of 5). Compound 1 reacts with di‐exo‐3‐aminobicyclo[2.2.1]heptane‐2‐methanamine (11) and di‐exo‐3‐aminobicyclo[2.2.1]hept‐5‐ene‐2‐methanamine (12) to give the methylene‐bridged pyrrolo[2,1‐b]quinazolinones 13 and 14 respectively; a pentacyclic product containing a dipyrrolodiazepine moiety 15 was also isolated. The structures and stereochemistry were elucidated by means of IR and NMR spectroscopy, including COSY, DIFFNOE, DEPT, HMQC and HMBC techniques.
📜 SIMILAR VOLUMES
Synthesis of Chiral Triamines and Diamines from Amino Acids. -The methodology is free of racemization and opens a facile way to selectively protected chiral di-and triamines. -(KOKOTOS, G.; MARKIDIS, T.;