Premium
The contrasting behavior of cyclic and acyclic 2‐amidomethyleneresorcinols towards cyclization with acetaldehyde
Author(s) -
Zaugg H. E.,
Arendsen D. L.,
Egan R. S.
Publication year - 1979
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.5570160105
Subject(s) - chemistry , acetaldehyde , resorcinol , stereochemistry , organic chemistry , ethanol
The two cyclic amidomethylene resorcinols, 3a and 3b , readily undergo cyclization with acetaldehyde to the azacannabinoids 4 and 6 , respectively. However, the acyclic amidomethylene resorcinol 10 , under the same conditions, gives the benzodioxan 11 . This contrasting behavior is rationalized in terms of conformational differences between 3a,b and 10 .
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom