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Synthesis of perhydro‐2(1 H )‐quinoxalinones and perhydropyrrolo[1,2‐ a ]quinoxalin‐4(5 H )‐one derivatives
Author(s) -
Rees David C.
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240512
Subject(s) - chemistry , bicyclic molecule , glycine , aziridine , ring (chemistry) , stereochemistry , carbamate , curtius rearrangement , tricyclic , proline , alanine , urea , amino acid , organic chemistry , biochemistry
The novel trans ‐bicyclic‐perhydro‐2(1 H )‐quinoxalinones 4, 6 and 7 and the tricyclic‐perhydropyrrolo[1,2‐ a ]‐quinoxalin‐4(5 H )‐one derivatives 8 and 9 are prepared via a ring opening and spontaneous ring closing reaction of the aziridines 2 and 3 with the α‐amino acids glycine, L‐alanine, L‐proline and L‐phenylalanine. This methodology was used to prepare 5 and 10 which are novel rigid analogues of the kappa opioid compound 1. Treatment of aziridine 3 with methyl carbamate gave the cyclic urea 11.