63191-54-8

Upstream product

• 288-32-4 1H-imidazole 
• 5469-26-1 1-Bromopinacolon 
• 13547-70-1 1-chloro-3,3-dimethyl-butan-2-one 

Downstream Products

• 86503-40-4 (Z)-1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-4,4-dimethylpent-1-en-3-one 
• 86384-55-6 (E)-1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-4,4-dimethylpent-1-en-3-one 

Relevant academic research and scientific papers

Synthesis of aliphatic α-ketoamides from α-substituted methyl ketones: Via a Cu-catalyzed aerobic oxidative amidation

α-Ketoamides are an important key functional group and have been used as versatile and valuable intermediates and synthons in a variety of functional group transformations. Synthetic methods for making aryl α-ketoamides as drug candidates have been greatly improved through metal-catalyzed aerobic oxidative amidations. However, the preparation of alkyl α-ketoamides through metal-catalyzed aerobic oxidative amidations has not been reported because generating α-ketoamides from aliphatic ketones with two α-carbons theoretically provides two distinct α-ketoamides. Our strategy is to activate the α-carbon by introducing an N-substituent at one of the two α-positions. The key to this strategy is how heterocyclic compounds such as triazoles and imidazoles affect the selectivity of the synthesis of the alkyl α-ketoamides. From this basic concept, and by optimizing the reaction and elucidating the mechanism of the synthesis of aryl α-ketoamides via a copper-catalyzed aerobic oxidative amidation, we prepared fourteen aliphatic α-ketoamides in high yields (48-84%). This journal is

Structure-activity relationship of uniconazole, a potent inhibitor of ABA 8′-hydroxylase, with a focus on hydrophilic functional groups and conformation

The plant growth retardant S-(+)-uniconazole (UNI-OH) is a strong inhibitor of abscisic acid (ABA) 8′-hydroxylase, a key enzyme in the catabolism of ABA, a plant hormone involved in stress tolerance, stomatal closure, flowering, seed dormancy, and other physiological events. In the present study, we focused on the two polar sites of UNI-OH and synthesized 3- and 2″-modified analogs. Conformational analysis and an in vitro enzyme inhibition assay yielded new findings on the structure-activity relationship of UNI-OH: (1) by substituting imidazole for triazole, which increases affinity to heme iron, we identified a more potent compound, IMI-OH; (2) the polar group at the 3-position increases affinity for the active site by electrostatic or hydrogen-bonding interactions; (3) the conformer preference for a polar environment partially contributes to affinity for the active site. These findings should be useful for designing potent azole-containing specific inhibitors of ABA 8′-hydroxylase.

An efficient and convenient method for synthesis of 1-substituted imidazoles

A convenient method for the synthesis 1-substituted imidazoles was developed by the reaction of α-bromoketone with lithium imidazolide. The reaction gave the desired products in improved yields without the formation of 1,3-disubstituted imidazolium salts. Treatment of bromoacetaldehyde ethylene acetal, 2-(bromomethyl)tetrahydro-2H-pyran, and N-(bromomethyl)phthalimide with lithium imidazolide also gave the corresponding 1-substituted imidazole in good to excellent yields. Direct reaction of α-bromoketone with imidazole as control experiment afforded undesired 1,3-disubstituted imidazolium salts with the desired mono-substituted products.

Combating fungi with imidazolyl-vinyl ketones and carbinols

Imidazolyl-vinyl ketones or carbinols of the formula STR1 in which A represents a keto group or a CH(OH) grouping, R1 represents an alkyl or halogenoalkyl radical and R2 represents an alkyl radical, an optionally substituted cycloalkyl or cycloalkenyl radical, a halogenoalkyl, alkoxyalkyl, alkylmercaptoalkyl, dialkylaminoalkyl or hydroxyalkyl radical, an optionally substituted alkenyl, alkinyl or alkeninyl radical, a phenylalkyl radical which is optionally substituted in the alkyl part and in the phenyl part, an optionally substituted indenyl or fluorenyl radical or an optionally substituted diphenylmethyl or triphenylmethyl radical, or acid addition products and metal salt complexes thereof which possess fungicidal activity.