Meso-Substituted Corroles from Nitrosoalkenes and Dipyrromethanes

The synthesis of bilanes and hexapyrroles containing an oxime functionality, prepared by two and three consecutive hetero-Diels–Alder reactions (or conjugated additions) between nitrosoalkenes and dipyrromethanes, is described. Bilanes underwent oxidative macrocyclization to afford a new class of tr...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 85; no. 5; pp. 3328 - 3335
Main Authors Lopes, Susana M. M, Pinho e Melo, Teresa M. V. D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.03.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ELECTROCHEMISTRY
OXIDATION
ORGANIC-SYNTHESIS
COMPLEXES
AZOALKENES
PORPHYRIN
ON-WATER
DERIVATIVES
CANCER
Online AccessGet full text

Cover

More Information
Summary:The synthesis of bilanes and hexapyrroles containing an oxime functionality, prepared by two and three consecutive hetero-Diels–Alder reactions (or conjugated additions) between nitrosoalkenes and dipyrromethanes, is described. Bilanes underwent oxidative macrocyclization to afford a new class of trans-A2B-corroles. Porphyrins could also be obtained by reacting bilanes with aldehydes in the presence of trifluoroacetic acid, followed by an oxidative step.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03151