Domino Reaction of 2,4-Diyn-1-ols with 1,3-Dicarbonyl Compounds: Direct Access to Aryl/Heteroaryl-Fused Benzofurans and Indoles.

Organic Letters
Chada Raji ReddyRené Grée

Abstract

A domino propargylation/furanylation (intramolecular exo-dig-cyclization)/benzannulation reaction of 2,4-diyn-1-ols with 1,3-dicarbonyl compounds has been developed for the first time. This provides a novel and effective method for the preparation of aryl/heteroaryl-fused benzofurans from easily accessible starting materials in a single step. The methodology was extended to pyrrolyl-benzannulation to obtain aryl/heteroaryl-fused indoles. Further, application of this approach in the synthesis of eustifoline D and dictyodendrin structural frameworks has been demonstrated.

References

Feb 1, 1996·Chemical Reviews·Lutz F. Tietze
Jan 20, 2005·Bioconjugate Chemistry·Yunpeng YeSamuel Achilefu
Dec 25, 2008·Chemical Reviews·M Sameiro T Gonçalves
Sep 5, 2009·Bioorganic & Medicinal Chemistry·Rémy Le GuévelGilles Salbert
Mar 4, 2011·Chemical Society Reviews·Youtian TaoJingui Qin
Sep 24, 2011·Journal of Natural Products·James J La ClairMichael D Burkart
Jan 23, 2013·Bioorganic & Medicinal Chemistry·Minoru TanakaYuusaku Yokoyama
Feb 17, 2015·The Journal of Organic Chemistry·Tomonori IitsukaMasahiro Miura
Jan 25, 2017·Chemical Communications : Chem Comm·Chada Raji ReddyRavula Shravya
Feb 1, 2016·Chemical Science·Yujiro Hayashi
Dec 15, 2017·Organic & Biomolecular Chemistry·Bhavani Shankar Chinta, Beeraiah Baire
Mar 26, 2019·Chemistry, an Asian Journal·Aimee K ClarkeWilliam P Unsworth
Dec 21, 2019·The Journal of Organic Chemistry·Stuart AikenB Mark Heron

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