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AgOTf-catalyzed electrophilic cyclization of triynols with NXS: rapid synthesis of densely trisubstituted naphthalenes and quinolines.
Chem Asian J. 2014 Jan; 9(1):126-30.CA

Abstract

A silver triflate-catalyzed electrophilic cyclization reaction of acyclic triynols with NXS (X=I, Br) under mild conditions is reported. Three reactive functional groups, such as a carbonyl group, an alkyne group, and a halogen, could be selectively installed at the C1, C2, and C3 positions to obtain the naphthalene and quinoline products, respectively. The obtained densely trisubstituted products could be further transformed into more complex aromatic products by manipulating the alkynyl moiety and the other two functional groups as synthons.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Chen Z
Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry & Chemical Engineering, Jiangxi Normal University, Ziyang Road 99, Nanchang, Jiangxi 330022 (P.R. China). zchenjx@hotmail.com.
Jia X
No affiliation info available
Ye C
No affiliation info available
Qiu G
No affiliation info available
Wu J
No affiliation info available

MeSH

AlcoholsAlkynesBromosuccinimideCatalysisCyclizationMesylatesMolecular StructureNaphthalenesQuinolinesSuccinimidesTime Factors

Pub Type(s)

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

Language

eng

PubMed ID

24166868

Citation

Chen, Zhiyuan, et al. "AgOTf-catalyzed Electrophilic Cyclization of Triynols With NXS: Rapid Synthesis of Densely Trisubstituted Naphthalenes and Quinolines." Chemistry, an Asian Journal, vol. 9, no. 1, 2014, pp. 126-30.
Chen Z, Jia X, Ye C, et al. AgOTf-catalyzed electrophilic cyclization of triynols with NXS: rapid synthesis of densely trisubstituted naphthalenes and quinolines. Chem Asian J. 2014;9(1):126-30.
Chen, Z., Jia, X., Ye, C., Qiu, G., & Wu, J. (2014). AgOTf-catalyzed electrophilic cyclization of triynols with NXS: rapid synthesis of densely trisubstituted naphthalenes and quinolines. Chemistry, an Asian Journal, 9(1), 126-30. https://doi.org/10.1002/asia.201301186
Chen Z, et al. AgOTf-catalyzed Electrophilic Cyclization of Triynols With NXS: Rapid Synthesis of Densely Trisubstituted Naphthalenes and Quinolines. Chem Asian J. 2014;9(1):126-30. PubMed PMID: 24166868.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - AgOTf-catalyzed electrophilic cyclization of triynols with NXS: rapid synthesis of densely trisubstituted naphthalenes and quinolines. AU - Chen,Zhiyuan, AU - Jia,Xuegong, AU - Ye,Changqing, AU - Qiu,Guanyinsheng, AU - Wu,Jie, Y1 - 2013/10/24/ PY - 2013/09/01/received PY - 2013/10/30/entrez PY - 2013/10/30/pubmed PY - 2015/1/6/medline KW - electrophilic cyclization KW - heterocycles KW - homogeneous catalysis KW - silver triflate KW - triynol SP - 126 EP - 30 JF - Chemistry, an Asian journal JO - Chem Asian J VL - 9 IS - 1 N2 - A silver triflate-catalyzed electrophilic cyclization reaction of acyclic triynols with NXS (X=I, Br) under mild conditions is reported. Three reactive functional groups, such as a carbonyl group, an alkyne group, and a halogen, could be selectively installed at the C1, C2, and C3 positions to obtain the naphthalene and quinoline products, respectively. The obtained densely trisubstituted products could be further transformed into more complex aromatic products by manipulating the alkynyl moiety and the other two functional groups as synthons. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/24166868/AgOTf_catalyzed_electrophilic_cyclization_of_triynols_with_NXS:_rapid_synthesis_of_densely_trisubstituted_naphthalenes_and_quinolines_ L2 - https://doi.org/10.1002/asia.201301186 DB - PRIME DP - Unbound Medicine ER -