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Zn(OTf)2-catalyzed cyclization of proparyl alcohols with anilines, phenols, and amides for synthesis of indoles, benzofurans, and oxazoles through different annulation mechanisms.
J Org Chem. 2006 Jun 23; 71(13):4951-5.JO

Abstract

Zn(OTf)2 (10 mol %) catalyzed the cyclization of propargyl alcohols with PhXH (X = O, NH) in hot toluene (100 degrees C) without additive and gave indole and benzofuran products with different structures. In such transformations, alpha-carbonyl intermediates A and C were isolated as reaction intermediates. The 1,2-nitrogen shift in the formation of indole is catalyzed by Zn(OTf)2, and its mechanism has been elucidated. This catalytic cyclization is also applicable to the synthesis of oxazoles through the cyclization of propargyl alcohols and amides without a 1,2-nitrogen shift.

Authors+Show Affiliations

Kumar MP
Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan 30043.
Liu RS
No affiliation info available

MeSH

AlcoholsAmidesAniline CompoundsBenzofuransCatalysisCyclizationIndolesMesylatesMolecular StructureOxazolesPhenolsStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16776526

Citation

Kumar, Manyam Praveen, and Rai-Shung Liu. "Zn(OTf)2-catalyzed Cyclization of Proparyl Alcohols With Anilines, Phenols, and Amides for Synthesis of Indoles, Benzofurans, and Oxazoles Through Different Annulation Mechanisms." The Journal of Organic Chemistry, vol. 71, no. 13, 2006, pp. 4951-5.
Kumar MP, Liu RS. Zn(OTf)2-catalyzed cyclization of proparyl alcohols with anilines, phenols, and amides for synthesis of indoles, benzofurans, and oxazoles through different annulation mechanisms. J Org Chem. 2006;71(13):4951-5.
Kumar, M. P., & Liu, R. S. (2006). Zn(OTf)2-catalyzed cyclization of proparyl alcohols with anilines, phenols, and amides for synthesis of indoles, benzofurans, and oxazoles through different annulation mechanisms. The Journal of Organic Chemistry, 71(13), 4951-5.
Kumar MP, Liu RS. Zn(OTf)2-catalyzed Cyclization of Proparyl Alcohols With Anilines, Phenols, and Amides for Synthesis of Indoles, Benzofurans, and Oxazoles Through Different Annulation Mechanisms. J Org Chem. 2006 Jun 23;71(13):4951-5. PubMed PMID: 16776526.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Zn(OTf)2-catalyzed cyclization of proparyl alcohols with anilines, phenols, and amides for synthesis of indoles, benzofurans, and oxazoles through different annulation mechanisms. AU - Kumar,Manyam Praveen, AU - Liu,Rai-Shung, PY - 2006/6/17/pubmed PY - 2007/6/28/medline PY - 2006/6/17/entrez SP - 4951 EP - 5 JF - The Journal of organic chemistry JO - J Org Chem VL - 71 IS - 13 N2 - Zn(OTf)2 (10 mol %) catalyzed the cyclization of propargyl alcohols with PhXH (X = O, NH) in hot toluene (100 degrees C) without additive and gave indole and benzofuran products with different structures. In such transformations, alpha-carbonyl intermediates A and C were isolated as reaction intermediates. The 1,2-nitrogen shift in the formation of indole is catalyzed by Zn(OTf)2, and its mechanism has been elucidated. This catalytic cyclization is also applicable to the synthesis of oxazoles through the cyclization of propargyl alcohols and amides without a 1,2-nitrogen shift. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/16776526/Zn_OTf_2_catalyzed_cyclization_of_proparyl_alcohols_with_anilines_phenols_and_amides_for_synthesis_of_indoles_benzofurans_and_oxazoles_through_different_annulation_mechanisms_ DB - PRIME DP - Unbound Medicine ER -