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Gold-catalyzed three-component annulation: efficient synthesis of highly functionalized dihydropyrazoles from alkynes, hydrazines, and aldehydes or ketones.
Org Lett. 2012 Jan 06; 14(1):326-9.OL

Abstract

Polysubstituted dihydropyrazoles were directly obtained by a gold-catalyzed three-component annulation. This reaction consists of a Mannich-type coupling of alkynes with N,N'-disubstituted hydrazines and aldehydes/ketones followed by intramolecular hydroamination. Cascade cyclization using 1,2-dialkynylbenzene derivatives as the alkyne component was also performed producing fused tricyclic dihydropyrazoles in good yields.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Suzuki Y
Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan.
Naoe S
No affiliation info available
Oishi S
No affiliation info available
Fujii N
No affiliation info available
Ohno H
No affiliation info available

MeSH

AldehydesAlkynesCatalysisCyclizationGoldHydrazinesHydrogenationKetonesMolecular StructurePyrazoles

Pub Type(s)

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

Language

eng

PubMed ID

22176630

Citation

Suzuki, Yamato, et al. "Gold-catalyzed Three-component Annulation: Efficient Synthesis of Highly Functionalized Dihydropyrazoles From Alkynes, Hydrazines, and Aldehydes or Ketones." Organic Letters, vol. 14, no. 1, 2012, pp. 326-9.
Suzuki Y, Naoe S, Oishi S, et al. Gold-catalyzed three-component annulation: efficient synthesis of highly functionalized dihydropyrazoles from alkynes, hydrazines, and aldehydes or ketones. Org Lett. 2012;14(1):326-9.
Suzuki, Y., Naoe, S., Oishi, S., Fujii, N., & Ohno, H. (2012). Gold-catalyzed three-component annulation: efficient synthesis of highly functionalized dihydropyrazoles from alkynes, hydrazines, and aldehydes or ketones. Organic Letters, 14(1), 326-9. https://doi.org/10.1021/ol203072u
Suzuki Y, et al. Gold-catalyzed Three-component Annulation: Efficient Synthesis of Highly Functionalized Dihydropyrazoles From Alkynes, Hydrazines, and Aldehydes or Ketones. Org Lett. 2012 Jan 6;14(1):326-9. PubMed PMID: 22176630.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Gold-catalyzed three-component annulation: efficient synthesis of highly functionalized dihydropyrazoles from alkynes, hydrazines, and aldehydes or ketones. AU - Suzuki,Yamato, AU - Naoe,Saori, AU - Oishi,Shinya, AU - Fujii,Nobutaka, AU - Ohno,Hiroaki, Y1 - 2011/12/16/ PY - 2011/12/20/entrez PY - 2011/12/20/pubmed PY - 2012/4/18/medline SP - 326 EP - 9 JF - Organic letters JO - Org Lett VL - 14 IS - 1 N2 - Polysubstituted dihydropyrazoles were directly obtained by a gold-catalyzed three-component annulation. This reaction consists of a Mannich-type coupling of alkynes with N,N'-disubstituted hydrazines and aldehydes/ketones followed by intramolecular hydroamination. Cascade cyclization using 1,2-dialkynylbenzene derivatives as the alkyne component was also performed producing fused tricyclic dihydropyrazoles in good yields. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/22176630/Gold_catalyzed_three_component_annulation:_efficient_synthesis_of_highly_functionalized_dihydropyrazoles_from_alkynes_hydrazines_and_aldehydes_or_ketones_ L2 - https://doi.org/10.1021/ol203072u DB - PRIME DP - Unbound Medicine ER -