Search

Here, we report highly efficient deoxygenative chlorination of aldehydes and alcohols with a dichloromethyl methyl ether and TiCl4 system. The method converts various aldehydes and alcohols into the desired geminal dichlorides or chlorides with good to excellent yields (up to 99 %). Combined with a subsequent Rieche formylation step using the same reagent system, this method provides an efficient approach for synthesis of aromatic dialdehydes. This strategy involves deoxy‐chlorination of the aryl aldehydes followed by a second formylation of more activated benzal chloride derivatives. Dialdehydes can be easily obtained by hydrolyzing the corresponding of dichloromethyl derivative. [ABSTRACT FROM AUTHOR]

Here, we report highly efficient deoxygenative chlorination of aldehydes and alcohols with a dichloromethyl methyl ether and TiCl4 system. The method converts various aldehydes and alcohols into the desired geminal dichlorides or chlorides with good to excellent yields (up to 99 %). Combined with a subsequent Rieche formylation step using the same reagent system, this method provides an efficient approach for synthesis of aromatic dialdehydes. This strategy involves deoxy‐chlorination of the aryl aldehydes followed by a second formylation of more activated benzal chloride derivatives. Dialdehydes can be easily obtained by hydrolyzing the corresponding of dichloromethyl derivative. [ABSTRACT FROM AUTHOR]

Abstract: A series of (1S,1′S)-4,4′-biquinazoline-based primary amines were prepared from natural amino acids via a six-step reaction sequence of protection and condensation followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection. These novel amines were screened for the asymmetric ethylation of aryl aldehydes to yield alcohols with an (S)-configuration with enantiomeric excesses (ee) varying from 2% to 95%. [Copyright &y& Elsevier]

Abstract: A simple synthetic method for the preparation of enantiomerically pure (S)-4-aminoquinazoline alcohols from (S)-quinazolinone alcohols by key steps including chlorination, nucleophilic ipso substitution, and deacetylation is presented. Mutagenic and antimutagenic properties of the (S)-4-aminoquinazoline alcohols were investigated by using Salmonella typhimurium TA1535, and Escherichia coli WP2uvrA tester strains at 0.01, 0.1, and 1μg/plate concentrations. (S)-4-aminoquinazoline alcohols were found to be genotoxically safe at the tested concentrations. Among the tested (S)-4-aminoquinazoline alcohols, the best antimutagenic activity was obtained with a methyl derivative at 0.1μg/plate dose. [ABSTRACT FROM AUTHOR]