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January 12, 2006The Journal of Organic Chemistry

Diversity-Oriented Synthesis of 3-Iodochromones and Heteroatom Analogues via ICl-Induced Cyclization

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Authors

CZChengxiang ZhouADAnton V. DubrovskyRLRichard C. Larock

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Overview

Experimental study demonstrates efficient ICl-induced cyclization of alkynones into 3-iodochromones, highlighting versatile access to complex heterocyclic scaffolds.

Key Points

  • Develop an efficient, mild synthetic method to construct 3-iodochromones and related heteroatom derivatives using iodine monochloride-promoted cyclization.
  • Subjected heteroatom-substituted alkynones to iodine monochloride (ICl)-mediated cyclization under mild reaction conditions.
  • Coupled the resulting iodinated heterocycles to secondary palladium-catalyzed reactions to introduce molecular complexity across varied scaffold types.
  • ICl-induced cyclization tolerated diverse functional groups and consistently delivered target chromones in good to excellent yields.
  • The cyclization framework effectively generalized to iodothiochromenones and iodoquinolinones, enabling rapid diversification into complex furans and polycyclic systems.

Cite This Study

Zhou et al. (2006) studied this question.

synapsesocial.com/papers/6a94cb3953e09118be7c3bebhttps://doi.org/10.1021/jo0523722
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