Assistant Professor of Chemistry Nicole L. Snyder and Christopher J. Boisvert ’12 recently published a chapter on the Hantzch Reaction in Named Reactions in Heterocyclic Chemistry II, one of the books in Jie Jack Li’s Named Organic Reaction series.
The Hantzsch Reaction is a condensation reaction that has been used to generate pyrroles, thiazoles and dihydropyridine derivatives. While the Hantzch pyrrole synthesis has shown limited use in recent years, the Hantzch thiazole and dihydropyridine syntheses have been extensively employed in the preparation of therapeutics. For example, the Hantzsch thiazole synthesis has been used to prepare novel antimalarial, antitumor and antibiotic compounds, as well as several thiopeptide-based natural products with antibiotic and/or antitumor activity. Recent examples of the latter include the synthesis of dolstatins 3 and 10, amythiamicin D, IB-01211, bistratamide H and thuggacin A1. The Hantzsch 1,4-dihydropyridine synthesis, which gained attention in the late 1960s with the synthesis of the potent calcium channel antagonist nifedipine, has since been used to generate more potent derivatives of nifedipine, as well as novel antibiotics such as micrococcin P1 and anticancer therapeutics such including an analog of monastrol.