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Expedient and Divergent Tandem One-Pot Synthesis of Benz[e]indole and Spiro[indene-1,3'-pyrrole] Derivatives from Alkyne-Tethered Chalcones/Cinnamates and TosMIC.
Org Lett. 2015 Jul 17; 17(14):3576-9.OL

Abstract

An efficient solvent-dependent regioselective [3 + 2]-cycloaddition/iodocyclization cascade reaction of alkyne-tethered chalcones/cinnamates and TosMIC has been developed. The reaction represents a novel protocol for the expedient and divergent one-pot synthesis of benz[e]indoles and spiro[indene-1,3'-pyrroles] from acyclic common precursors at room temperature.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhang X
†Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Feng C
†Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Jiang T
‡Vascular Surgery, China-Japan Union Hospital of Jilin University, Changchun 130033, China.
Li Y
†Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Pan L
†Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Xu X
†Department of Chemistry, Northeast Normal University, Changchun 130024, China.

MeSH

AlkynesCatalysisChalconesCinnamatesCyanidesCycloaddition ReactionIndolesPyrrolesSpiro CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

26154613

Citation

Zhang, Xue, et al. "Expedient and Divergent Tandem One-Pot Synthesis of Benz[e]indole and Spiro[indene-1,3'-pyrrole] Derivatives From Alkyne-Tethered Chalcones/Cinnamates and TosMIC." Organic Letters, vol. 17, no. 14, 2015, pp. 3576-9.
Zhang X, Feng C, Jiang T, et al. Expedient and Divergent Tandem One-Pot Synthesis of Benz[e]indole and Spiro[indene-1,3'-pyrrole] Derivatives from Alkyne-Tethered Chalcones/Cinnamates and TosMIC. Org Lett. 2015;17(14):3576-9.
Zhang, X., Feng, C., Jiang, T., Li, Y., Pan, L., & Xu, X. (2015). Expedient and Divergent Tandem One-Pot Synthesis of Benz[e]indole and Spiro[indene-1,3'-pyrrole] Derivatives from Alkyne-Tethered Chalcones/Cinnamates and TosMIC. Organic Letters, 17(14), 3576-9. https://doi.org/10.1021/acs.orglett.5b01676
Zhang X, et al. Expedient and Divergent Tandem One-Pot Synthesis of Benz[e]indole and Spiro[indene-1,3'-pyrrole] Derivatives From Alkyne-Tethered Chalcones/Cinnamates and TosMIC. Org Lett. 2015 Jul 17;17(14):3576-9. PubMed PMID: 26154613.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Expedient and Divergent Tandem One-Pot Synthesis of Benz[e]indole and Spiro[indene-1,3'-pyrrole] Derivatives from Alkyne-Tethered Chalcones/Cinnamates and TosMIC. AU - Zhang,Xue, AU - Feng,Chengjie, AU - Jiang,Tao, AU - Li,Yifei, AU - Pan,Ling, AU - Xu,Xianxiu, Y1 - 2015/07/08/ PY - 2015/7/9/entrez PY - 2015/7/15/pubmed PY - 2015/10/30/medline SP - 3576 EP - 9 JF - Organic letters JO - Org Lett VL - 17 IS - 14 N2 - An efficient solvent-dependent regioselective [3 + 2]-cycloaddition/iodocyclization cascade reaction of alkyne-tethered chalcones/cinnamates and TosMIC has been developed. The reaction represents a novel protocol for the expedient and divergent one-pot synthesis of benz[e]indoles and spiro[indene-1,3'-pyrroles] from acyclic common precursors at room temperature. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26154613/Expedient_and_Divergent_Tandem_One_Pot_Synthesis_of_Benz[e]indole_and_Spiro[indene_13'_pyrrole]_Derivatives_from_Alkyne_Tethered_Chalcones/Cinnamates_and_TosMIC_ DB - PRIME DP - Unbound Medicine ER -