Since its discovery over a century ago, oxalyl chloride remains to be widely commercially available, economical, and versatile reagent in organic synthesis. We recently reported a convenient two-step one-pot synthesis of symmetrical and unsymmetrical diacyl urea derivatives, acyl ureas/carbamates/thiocarbamates, and related compounds by using oxalyl chloride as a donor of carbonyl group. We utilized this methodology to design and synthesize a small library of urea- and carbamate-based inhibitors of fatty acid amide hydrolase (FAAH) as prospective modulators of the endocannabinoid system. We also expanded this methodology to prepare a panel of interesting small molecules with potential antiprotozoal activity. More recently, we employed oxalyl chloride to a convenient synthesis of the fungus-derived naturally occurring lipoids: N,N'-dipalmitoleyl urea (C16:1) and N,N'-dioleyl urea (C18:1), which are deemed to serve as a fungus-specific pathogen-associated molecules. Reaction of oxalyl chloride with various benzenesulfonohydrazides readily provided a set of molecules referred to as blowing agents. Overall, this presentation will showcase the versatility of oxalyl chloride in chemical transformations relevant to synthetic organic and medicinal chemistry as well as natural products synthesis (Figure 1).

Oxalyl chloride as a convenient donor of one and two carbonyl groups in chemical transformations

ACS Fall 2020 Virtual Meeting

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