Alkylation of 1,3-bis(benzotriazol-1-yl)propan-2-one with α-iodo ketones

Expeditious Syntheses to Pharmochemicals 1,3-Dihydroxyacetone, 1,3-Dichloro-, 1,3-Dibromo- and 1,3-Diiodoacetone from Glycerol 1,3-Dichlorohydrin Using Homogenous and Heterogenous Medium

“…On the other hand, 1,3-dihaloacetones are used in organic synthesis as versatile building blocks for more complex molecules. [44][45][46][47][48][49][50][51][52][53][54][55][56][57] Interestingly, they have been isolated from marine algae of the genus Asparagopsis taxiformis, A. armata and Falkenbergia rufolanosa. 58,59 The 1,3-dichloroacetone is used in the synthesis of famotidine and citric acid and as substrate in crossed aldol condensation reactions.…”

“…52 In addition, it is employed in organic synthesis for the construction of various heterocyclic systems through S-and N-alkylation reactions. [49][50][51] Many of these heterocyclic compounds exhibit analgesic, anti-inflammatory, antiviral, antihypertensive and antitumor activities. [49][50][51] Already, the 1,3-dibromoacetone (7) has been used as raw material in the quinaldine derivative synthesis, a drug used in the treatment of acute asthma.…”

“…[49][50][51] Many of these heterocyclic compounds exhibit analgesic, anti-inflammatory, antiviral, antihypertensive and antitumor activities. [49][50][51] Already, the 1,3-dibromoacetone (7) has been used as raw material in the quinaldine derivative synthesis, a drug used in the treatment of acute asthma. 45 In addition, compound 7 has been used in the synthesis of iminolactones (antibacterial), 46 aldosterone inhibitors, 47 vinylcyclopropane 47 and propranolol hydrochloride (a drug used for heart treatment).…”

Regio‐ and Chemoselectivity of Tandem N‐Ketoalkylation/Cyclization of 2‐Thioxoimidazoline‐4‐One

“…Earlier, we have shown that α-iodoketones, due to the high reactivity of the CÀ I bond, readily alkylate heterocyclic compounds with the carbonyl group in the molecule in the absence of bases or catalysts; the degree and regioselectivity of alkylation have also been investigated depending on the structure of the heterocycle. [35][36][37][38]…”

“…With this in mind, the aim of the present work was to investigate the reactions of thiohydantoin with aliphatic, aromatic, and heteroaromatic α‐iodoketones, and to explore the possibility of cyclization of the expected alkylation products. Earlier, we have shown that α‐iodoketones, due to the high reactivity of the C−I bond, readily alkylate heterocyclic compounds with the carbonyl group in the molecule in the absence of bases or catalysts; the degree and regioselectivity of alkylation have also been investigated depending on the structure of the heterocycle [35–38] …”