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Literature DB >> 16626117

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

Dawei Yue¹, Nicola Della Ca, Richard 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.

Entities: Chemical Gene

Mesh：

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Year: 2006 PMID： 16626117 PMCID： PMC2586152 DOI： 10.1021/jo0524573

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

25 in total

1. Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization.

Authors: Dawei Yue; Tuanli Yao; Richard C Larock
Journal: J Org Chem Date: 2005-12-09 Impact factor: 4.354

2. Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes.

Authors: Qinhua Huang; Jack A Hunter; Richard C Larock
Journal: J Org Chem Date: 2002-05-17 Impact factor: 4.354

3. A novel palladium-mediated coupling approach to 2,3-disubstituted benzo(b)thiophenes and its application to the synthesis of tubulin binding agents.

Authors: B L Flynn; P Verdier-Pinard; E Hamel
Journal: Org Lett Date: 2001-03-08 Impact factor: 6.005

4. Synthesis of Isocoumarins and alpha-Pyrones via Palladium-Catalyzed Annulation of Internal Alkynes.

Authors: Richard C. Larock; Mark J. Doty; Xiaojun Han
Journal: J Org Chem Date: 1999-11-26 Impact factor: 4.354

5. Synthesis of 2,3-disubstituted benzo[b]thiophenes via palladium-catalyzed coupling and electrophilic cyclization of terminal acetylenes.

Authors: Dawei Yue; Richard C Larock
Journal: J Org Chem Date: 2002-03-22 Impact factor: 4.354

6. Regioselective synthesis of substituted naphthalenes: a novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes.

Authors: José Barluenga; Henar Vázquez-Villa; Alfredo Ballesteros; José M González
Journal: Org Lett Date: 2003-10-30 Impact factor: 6.005

7. Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines.

Authors: Dawei Yue; Richard C Larock
Journal: Org Lett Date: 2004-03-18 Impact factor: 6.005

8. Efficient syntheses of heterocycles and carbocycles by electrophilic cyclization of acetylenic aldehydes and ketones.

Authors: Dawei Yue; Nicola Della Cà; Richard C Larock
Journal: Org Lett Date: 2004-05-13 Impact factor: 6.005

9. Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles: a versatile trigger for assembling oxygen heterocycles.

Authors: José Barluenga; Henar Vázquez-Villa; Alfredo Ballesteros; José M González
Journal: J Am Chem Soc Date: 2003-07-30 Impact factor: 15.419

10. Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes.

Authors: Naoki Asao; Tsutomu Nogami; Sunyoung Lee; Yoshinori Yamamoto
Journal: J Am Chem Soc Date: 2003-09-10 Impact factor: 15.419

10 in total

1. Tandem Cycloisomerization/Suzuki Coupling of Arylethynyl MIDA Boronates.

Authors: Julian M W Chan; Giovanni W Amarante; F Dean Toste
Journal: Tetrahedron Date: 2011-06-17 Impact factor: 2.457

2. Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu(4)NI-induced electrophilic cyclization.

Authors: Yu Chen; Chul-Hee Cho; Feng Shi; Richard C Larock
Journal: J Org Chem Date: 2009-09-04 Impact factor: 4.354

3. Iodine/palladium approaches to the synthesis of polyheterocyclic compounds.

Authors: Saurabh Mehta; Richard C Larock
Journal: J Org Chem Date: 2010-03-05 Impact factor: 4.354

4. A novel synthetic route to 3-sulfenyl- and 3-selenylindoles by n-Bu4NI-induced electrophilic cyclization.

Authors: Yu Chen; Chul-Hee Cho; Richard C Larock
Journal: Org Lett Date: 2009-01-01 Impact factor: 6.005

5. Competition studies in alkyne electrophilic cyclization reactions.

Authors: Saurabh Mehta; Jesse P Waldo; Richard C Larock
Journal: J Org Chem Date: 2009-02-06 Impact factor: 4.354

6. The synthesis of highly substituted isoxazoles by electrophilic cyclization: an efficient synthesis of valdecoxib.

Authors: Jesse P Waldo; Richard C Larock
Journal: J Org Chem Date: 2007-11-03 Impact factor: 4.354

7. A simple and mild synthesis of 1H-isochromenes and (Z)-1-alkylidene-1,3-dihydroisobenzofurans by the iodocyclization of 2-(1-alkynyl)benzylic alcohols.

Authors: Raffaella Mancuso; Saurabh Mehta; Bartolo Gabriele; Giuseppe Salerno; William S Jenks; Richard C Larock
Journal: J Org Chem Date: 2010-02-05 Impact factor: 4.354

8. Palladium mediated domino reaction: synthesis of isochromenes under aqueous medium.

Authors: Lavisha Punia; Karu Ramesh; Gedu Satyanarayana
Journal: RSC Adv Date: 2020-01-02 Impact factor: 4.036

9. Synthesis of 4-(1H-isochromen-1-yl)isoquinolines through the silver-catalysed homodimerization of ortho-alkynylarylaldehydes and subsequent condensation of the 1,5-dicarbonyl motif with NH₃.

Authors: Minghui Guo; Xin Meng; Yang Zhao; Yuexia Dong; Xuejun Sun; Laijin Tian; Ziping Cao
Journal: RSC Adv Date: 2019-01-21 Impact factor: 4.036

10. Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes.

Authors: An Wu; Hui Qian; Wanxiang Zhao; Jianwei Sun
Journal: Chem Sci Date: 2020-07-06 Impact factor: 9.825

10 in total