Item – Theses Canada

​
OCLC number
65420710
Link(s) to full text
LAC copy
LAC copy
Author
Wilson, Brian J.(Brian John),1974-
Title
Anionic ortho-fries rearrangement of N-carbamoyl diarylamines. Synthesis of the acridone alkaloid junosidine.
Degree
M. Sc. -- Queen's University at Kingston, 2004
Publisher
Ottawa : Library and Archives Canada = Bibliothèque et Archives Canada, [2005]
Description
2 microfiches.
Notes
Includes bibliographical references.
Abstract
The directed 'ortho' metalation (D' o'M) induced anionic rearrangement of 'N,N'-diaryl ureas 1.203 into 'N'-arylanthranilamides 1.204 and 1.205 (Scheme 1.55/Scheme 1.61) has been studied in detail. A highly regioselective 'N'-anionic 'ortho ' Fries rearrangement of unsymetrical 'N,N'-diaryl ureas has been developed ('Scheme 1.61') and a 'pseudo '-regiospecific version of this rearrangement for the synthesis of 1,2,3-trisubstituted 'N'-arylanthranilamides 1.210 (Scheme 1.58) has also been established. The synthetic utility of this new anionic 'ortho' Fries rearrangement has been demonstrated in the total synthesis of two acridone alkaloid natural products, yukodine 1.215 and junosidine 1.6 (Schemes 1.66 and 1.67) .
ISBN
0612997413
9780612997417