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Intramolecular diels‐alder reactions. 4 . Additions to naphthalene
Author(s) -
Ciganek Engelbert,
Wuonola Mark A.,
Harlow Richard L.
Publication year - 1994
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.5570310523
Subject(s) - chemistry , propynyl , intramolecular force , anthracene , naphthalene , derivative (finance) , medicinal chemistry , stereochemistry , lactam , diels–alder reaction , intramolecular reaction , organic chemistry , catalysis , financial economics , economics
N ‐Methyl‐ N ‐2‐propynyl‐1‐naphthalenecarboxamide, N ‐methyl‐ N ‐2‐propynyl‐1‐naphthaleneacetamide, and N ‐methyl‐ N ‐3‐butynyl‐1‐naphthalenecarboxamide undergo intramolecular Diels‐Alder reactions at 190°, 250°, and 270° to give lactams 1,6 , and 9 , respectively. The cyclization temperatures are higher by 80‐120° as compared to those of the corresponding anthracene derivatives. Elaboration of lactam 6 gave the trans ‐4a‐aryldecahydroisoquinoline derivative 7a which, as the (‐) isomer, was shown to have the same absolute stereochemistry as morphine.