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Thermally induced formal [3+2] cyclization of ortho-aminoaryl-tethered alkylidenecyclopropanes: facile synthesis of furoquinoline and thienoquinoline derivatives.
Chem Commun (Camb). 2016 Feb 14; 52(13):2701-4.CC

Abstract

We have developed a facile synthetic method to access furoquinoline and thienoquinoline derivatives via a thermally induced ring-opening and cyclization reaction from ortho-aminoaryl-tethered alkylidenecyclopropanes with the in situ generation of isocyanates or isothiocyanates. These reactions exhibited excellent yields and functional group tolerance under metal-free conditions.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yu LZ
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, China.
Hu XB
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, China.
Xu Q
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, China.
Shi M
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, China and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. mshi@mail.sioc.ac.cn.

MeSH

CyclizationCyclopropanesHot TemperatureQuinolines

Pub Type(s)

Journal Article

Language

eng

PubMed ID

26756044

Citation

Yu, Liu-Zhu, et al. "Thermally Induced Formal [3+2] Cyclization of Ortho-aminoaryl-tethered Alkylidenecyclopropanes: Facile Synthesis of Furoquinoline and Thienoquinoline Derivatives." Chemical Communications (Cambridge, England), vol. 52, no. 13, 2016, pp. 2701-4.
Yu LZ, Hu XB, Xu Q, et al. Thermally induced formal [3+2] cyclization of ortho-aminoaryl-tethered alkylidenecyclopropanes: facile synthesis of furoquinoline and thienoquinoline derivatives. Chem Commun (Camb). 2016;52(13):2701-4.
Yu, L. Z., Hu, X. B., Xu, Q., & Shi, M. (2016). Thermally induced formal [3+2] cyclization of ortho-aminoaryl-tethered alkylidenecyclopropanes: facile synthesis of furoquinoline and thienoquinoline derivatives. Chemical Communications (Cambridge, England), 52(13), 2701-4. https://doi.org/10.1039/c5cc09218c
Yu LZ, et al. Thermally Induced Formal [3+2] Cyclization of Ortho-aminoaryl-tethered Alkylidenecyclopropanes: Facile Synthesis of Furoquinoline and Thienoquinoline Derivatives. Chem Commun (Camb). 2016 Feb 14;52(13):2701-4. PubMed PMID: 26756044.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Thermally induced formal [3+2] cyclization of ortho-aminoaryl-tethered alkylidenecyclopropanes: facile synthesis of furoquinoline and thienoquinoline derivatives. AU - Yu,Liu-Zhu, AU - Hu,Xu-Bo, AU - Xu,Qin, AU - Shi,Min, PY - 2016/1/13/entrez PY - 2016/1/13/pubmed PY - 2016/10/7/medline SP - 2701 EP - 4 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 52 IS - 13 N2 - We have developed a facile synthetic method to access furoquinoline and thienoquinoline derivatives via a thermally induced ring-opening and cyclization reaction from ortho-aminoaryl-tethered alkylidenecyclopropanes with the in situ generation of isocyanates or isothiocyanates. These reactions exhibited excellent yields and functional group tolerance under metal-free conditions. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/26756044/Thermally_induced_formal_[3+2]_cyclization_of_ortho_aminoaryl_tethered_alkylidenecyclopropanes:_facile_synthesis_of_furoquinoline_and_thienoquinoline_derivatives_ DB - PRIME DP - Unbound Medicine ER -