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Chemoselective synthesis of polycyclic spiroindolines and polysubstituted pyrroles via the domino reaction of 2-isocyanoethylindoles.
J Org Chem. 2014 Sep 19; 79(18):8577-83.JO

Abstract

Chemoselective 2-isocyanoethylindole-based domino reactions for the construction of polycyclic spiroindoline derivatives and polysubstituted pyrroles have been developed. The reaction of 2-isocyanoethylindoles and gem-diactivated olefins lead to the polycyclic spiroindoline derivatives (up to 92% yields) in EtOH under reflux conditions. Furthermore, the three-component reaction of 2-isocyanoethylindoles with gem-diactivated olefins and secondary amines afford polysubstituted pyrroles (in moderate yields) in CH3CN under reflux conditions.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wang X
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University , Suzhou 215123, China.
Wang SY
No affiliation info available
Ji SJ
No affiliation info available

MeSH

CatalysisIndolesMolecular StructureNitrilesPolycyclic Aromatic HydrocarbonsPyrrolesSpiro Compounds

Pub Type(s)

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

Language

eng

PubMed ID

25148250

Citation

Wang, Xiang, et al. "Chemoselective Synthesis of Polycyclic Spiroindolines and Polysubstituted Pyrroles Via the Domino Reaction of 2-isocyanoethylindoles." The Journal of Organic Chemistry, vol. 79, no. 18, 2014, pp. 8577-83.
Wang X, Wang SY, Ji SJ. Chemoselective synthesis of polycyclic spiroindolines and polysubstituted pyrroles via the domino reaction of 2-isocyanoethylindoles. J Org Chem. 2014;79(18):8577-83.
Wang, X., Wang, S. Y., & Ji, S. J. (2014). Chemoselective synthesis of polycyclic spiroindolines and polysubstituted pyrroles via the domino reaction of 2-isocyanoethylindoles. The Journal of Organic Chemistry, 79(18), 8577-83. https://doi.org/10.1021/jo501143m
Wang X, Wang SY, Ji SJ. Chemoselective Synthesis of Polycyclic Spiroindolines and Polysubstituted Pyrroles Via the Domino Reaction of 2-isocyanoethylindoles. J Org Chem. 2014 Sep 19;79(18):8577-83. PubMed PMID: 25148250.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chemoselective synthesis of polycyclic spiroindolines and polysubstituted pyrroles via the domino reaction of 2-isocyanoethylindoles. AU - Wang,Xiang, AU - Wang,Shun-Yi, AU - Ji,Shun-Jun, Y1 - 2014/09/03/ PY - 2014/8/23/entrez PY - 2014/8/26/pubmed PY - 2015/2/28/medline SP - 8577 EP - 83 JF - The Journal of organic chemistry JO - J Org Chem VL - 79 IS - 18 N2 - Chemoselective 2-isocyanoethylindole-based domino reactions for the construction of polycyclic spiroindoline derivatives and polysubstituted pyrroles have been developed. The reaction of 2-isocyanoethylindoles and gem-diactivated olefins lead to the polycyclic spiroindoline derivatives (up to 92% yields) in EtOH under reflux conditions. Furthermore, the three-component reaction of 2-isocyanoethylindoles with gem-diactivated olefins and secondary amines afford polysubstituted pyrroles (in moderate yields) in CH3CN under reflux conditions. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/25148250/Chemoselective_synthesis_of_polycyclic_spiroindolines_and_polysubstituted_pyrroles_via_the_domino_reaction_of_2_isocyanoethylindoles_ DB - PRIME DP - Unbound Medicine ER -