CARBON-CARBON BOND-CLEAVAGE OF ALPHA-HYDROXYBENZYLHETEROARENES TO KETONES AND HETEROARENES BY CATALYTIC ACTION OF CYANIDE ION BASED ON RETROBENZOIN CONDENSATION

Authors
MIYASHITA A SUZUKI Y TAKEMURA Y IWAMOTO K HIGASHINO T
Citation
A. Miyashita et al., CARBON-CARBON BOND-CLEAVAGE OF ALPHA-HYDROXYBENZYLHETEROARENES TO KETONES AND HETEROARENES BY CATALYTIC ACTION OF CYANIDE ION BASED ON RETROBENZOIN CONDENSATION, Heterocycles, 45(1), 1997, pp. 1-5
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
45
Issue
1
Year of publication
1997
Pages
1 - 5
Database
ISI
SICI code
0385-5414(1997)45:1<1:CBOATK>2.0.ZU;2-1
Abstract
Treatment of 4-(alpha-benzyl-alpha-hydroxybenzyl)quinazoline (2a) with potassium cyanide in DMF resulted in carbon-carbon bond cleavage to g ive benzyl phenyl ketone (3a) and quinazoline (4). Similar results wer e obtained with other 4-(alpha-hydroxybenzyl)quinazolines (2b-f and 7a ). This reaction proceeds through retrobenzoin condensation. This cond ensation also proceeded in pyrazolopyrimidine (9a) triazolopyrimidine (10a), quinoxaline (11a), and benzimidazole (12a), and the imidazolium salt (16) was an effective catalyst.