An Alkyne–Isocyanide Cycloaddition/Boulton-Katritzky Rearrangement/Ring Expansion Reaction: Access to 9-Deazaguanines
Jianghao Luo, Haowen Ma, Kaifu Wu, Yun‐Lin Ao, Wei Zhou, Qian Cai
Abstract
An alkyne-isocyanide [3 + 2] cycloaddition followed by a Boulton-Katritzky rearrangement and a ring expansion is demonstrated. Different from the typical Boulton-Katritzky rearrangement, which forms five-membered ring products, the rearrangement-ring expansion method provides a mild, efficient, and atom-economical access to fused 9-deazaguanine structures in high yields.
Topics & Concepts
ChemistryRing (chemistry)CycloadditionIsocyanideAlkyneRearrangement reactionCombinatorial chemistryStereochemistryCatalysisOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsClick Chemistry and Applications