Gang Yan, B. Zekarias, Xiaoyu Li
Jan 7, 2020
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Influential Citations
12
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Journal
Chemistry
Abstract
A highly efficient 2-chloroquinazolin-4(3 H )-one rearrangement was developed that predictably generates either twisted-cyclic or ring-fused guanidines in a single operation, depending on the presence of a primary versus secondary amine in the accompanying diamine reagent. Exclusive formation of twisted-cyclic guanidines results from pairing 2-chloroquinazolinones with secondary diamines. Use of primary amine-containing diamines permits a domino quinazolinone rearrangement/intramolecular cyclization, gated through ( E )-twisted-cyclic guanidines, to afford ring-fused N -acylguanidines. This scalable, structurally tolerant transformation generated 55 guanidines and delivered twisted-cyclic guanidines with robust plasma stability and an abbreviated total synthesis of an antitumor ring-fused guanidine (4 steps, 55% yield).