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Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes.
J Org Chem. 2006 Jan 06; 71(1):236-43.JO

Abstract

[reactions: see text] A wide variety of substituted naphthalenes are readily prepared regioselectively under mild reaction conditions by the 6-endo-dig electrophilic cyclization of appropriate arene-containing propargylic alcohols by ICl, I2, Br2, NBS, and PhSeBr. 3-Iodo-2-naphthols have also been prepared in excellent yields by the cyclization of analogous 1-aryl-3-alkyn-2-ones. This methodology readily accommodates various functional groups and has been successfully extended to the synthesis of substituted carbazoles and dibenzothiophenes.

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Authors+Show Affiliations

Zhang X
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Sarkar S
No affiliation info available
Larock RC
No affiliation info available

MeSH

AlkynesCatalysisCyclizationElectronsMolecular StructureNaphthalenesNaphthols

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

16388642

Citation

Zhang, Xiaoxia, et al. "Synthesis of Naphthalenes and 2-naphthols By the Electrophilic Cyclization of Alkynes." The Journal of Organic Chemistry, vol. 71, no. 1, 2006, pp. 236-43.
Zhang X, Sarkar S, Larock RC. Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes. J Org Chem. 2006;71(1):236-43.
Zhang, X., Sarkar, S., & Larock, R. C. (2006). Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes. The Journal of Organic Chemistry, 71(1), 236-43.
Zhang X, Sarkar S, Larock RC. Synthesis of Naphthalenes and 2-naphthols By the Electrophilic Cyclization of Alkynes. J Org Chem. 2006 Jan 6;71(1):236-43. PubMed PMID: 16388642.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes. AU - Zhang,Xiaoxia, AU - Sarkar,Sampa, AU - Larock,Richard C, PY - 2006/1/4/pubmed PY - 2006/7/27/medline PY - 2006/1/4/entrez SP - 236 EP - 43 JF - The Journal of organic chemistry JO - J Org Chem VL - 71 IS - 1 N2 - [reactions: see text] A wide variety of substituted naphthalenes are readily prepared regioselectively under mild reaction conditions by the 6-endo-dig electrophilic cyclization of appropriate arene-containing propargylic alcohols by ICl, I2, Br2, NBS, and PhSeBr. 3-Iodo-2-naphthols have also been prepared in excellent yields by the cyclization of analogous 1-aryl-3-alkyn-2-ones. This methodology readily accommodates various functional groups and has been successfully extended to the synthesis of substituted carbazoles and dibenzothiophenes. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/16388642/Synthesis_of_naphthalenes_and_2_naphthols_by_the_electrophilic_cyclization_of_alkynes_ DB - PRIME DP - Unbound Medicine ER -