Syntheses of isochromenes and naphthalenes by electrophilic cyclization of acetylenic arenecarboxaldehydes.

The Journal of Organic Chemistry
Dawei YueRichard C Larock

Abstract

Highly substituted 1H-isochromenes, isobenzofurans, and pyranopyridines can be prepared by allowing o-(1-alkynyl)arenecarboxaldehydes and ketones to react with I2, ICl, NIS, Br2, NBS, p-O2NC6H4SCl, or PhSeBr and various alcohols or carbon-based nucleophiles at room temperature. Naphthyl ketones and iodides are also readily prepared by the reaction of 2-(1-alkynyl)arenecarboxaldehydes with I2 and simple olefins or alkynes.

References

Oct 12, 2000·Angewandte Chemie·A Dömling, I Ugi
Oct 25, 2001·The Journal of Organic Chemistry·Richard C. LarockXiaojun Han
May 11, 2002·The Journal of Organic Chemistry·Qinhua HuangRichard C Larock
Oct 24, 2002·Journal of the American Chemical Society·Naoki AsaoYoshinori Yamamoto
Jul 19, 2003·The Journal of Organic Chemistry·Tuanli Yao, Richard C Larock
Jul 30, 2004·Organic Letters·Tuanli YaoRichard C Larock
Feb 12, 2005·The Journal of Organic Chemistry·Tuanli Yao, Richard C Larock
Feb 25, 2005·Organic Letters·Xiaoxia ZhangRichard C Larock
Apr 23, 2005·The Journal of Organic Chemistry·Tuanli YaoRichard C Larock
Sep 1, 2005·Journal of the American Chemical Society·Xiaoxia Zhang, Richard C Larock
Nov 15, 2005·Journal of Combinatorial Chemistry·Tuanli YaoRichard C Larock

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Citations

Jul 29, 2011·ACS Combinatorial Science·Trapti AggarwalAkhilesh K Verma
Nov 6, 2007·The Journal of Organic Chemistry·Jesse P Waldo, Richard C Larock
Dec 25, 2008·The Journal of Organic Chemistry·Saurabh MehtaRichard C Larock
Feb 4, 2010·The Journal of Organic Chemistry·Saurabh Mehta, Richard C Larock
May 8, 2010·Chemical Communications : Chem Comm·Yoshinori YamamotoTienan Jin
Oct 27, 2015·The Journal of Organic Chemistry·Maciej E DomaradzkiYu Chen
Nov 29, 2014·Organic & Biomolecular Chemistry·Shifa ZhuHuanfeng Jiang
Jul 8, 2016·Organic & Biomolecular Chemistry·Trapti AggarwalAkhilesh K Verma
Mar 25, 2011·Chemistry : a European Journal·Fang YangYong-Min Liang
Sep 12, 2009·Chemistry : a European Journal·Riccardo EgrisJ Carlos Menéndez
Dec 31, 2008·Angewandte Chemie·Akhilesh Kumar VermaRichard C Larock
May 19, 2010·Angewandte Chemie·Benedikt CroneKlaus-Daniel Umland
Jun 6, 2015·Chemistry : a European Journal·Rohan VolpeBernard L Flynn
May 19, 2017·Organic & Biomolecular Chemistry·Sonu KumarAkhilesh K Verma
Feb 12, 2013·Organic & Biomolecular Chemistry·Thangavel Selvi, Kannupal Srinivasan
Mar 11, 2020·The Journal of Organic Chemistry·Esra Korkmaz, Metin Zora
Mar 7, 2008·The Journal of Organic Chemistry·Ziwei W Just, Richard C Larock

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