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Lewis or Brønsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif.
Org Biomol Chem. 2019 12 18; 18(1):135-139.OB

Abstract

We developed a facile synthetic method to access cyclopenta[b]naphthalene derivatives via the Lewis or Brønsted acid catalysed cascade nucleophilic addition, electronic cyclization, ring-opening rearrangement of propargylic alcohol-tethered alkylidenecyclopropanes with indole and pyrrole derivatives. The reaction exhibited a broad substrate scope and good functional group tolerance under metal-free conditions, affording the desired products in moderate to good yields.

Authors+Show Affiliations

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

31803894

Citation

Wei, Hao-Zhao, et al. "Lewis or Brønsted Acid-catalysed Reaction of Propargylic Alcohol-tethered Alkylidenecyclopropanes With Indoles and Pyrroles for the Preparation of Polycyclic Compounds Tethered With Indole or Pyrrole Motif." Organic & Biomolecular Chemistry, vol. 18, no. 1, 2019, pp. 135-139.
Wei HZ, Yu LZ, Shi M. Lewis or Brønsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif. Org Biomol Chem. 2019;18(1):135-139.
Wei, H. Z., Yu, L. Z., & Shi, M. (2019). Lewis or Brønsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif. Organic & Biomolecular Chemistry, 18(1), 135-139. https://doi.org/10.1039/c9ob02211b
Wei HZ, Yu LZ, Shi M. Lewis or Brønsted Acid-catalysed Reaction of Propargylic Alcohol-tethered Alkylidenecyclopropanes With Indoles and Pyrroles for the Preparation of Polycyclic Compounds Tethered With Indole or Pyrrole Motif. Org Biomol Chem. 2019 12 18;18(1):135-139. PubMed PMID: 31803894.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lewis or Brønsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif. AU - Wei,Hao-Zhao, AU - Yu,Liu-Zhu, AU - Shi,Min, PY - 2019/12/6/pubmed PY - 2019/12/6/medline PY - 2019/12/6/entrez SP - 135 EP - 139 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 18 IS - 1 N2 - We developed a facile synthetic method to access cyclopenta[b]naphthalene derivatives via the Lewis or Brønsted acid catalysed cascade nucleophilic addition, electronic cyclization, ring-opening rearrangement of propargylic alcohol-tethered alkylidenecyclopropanes with indole and pyrrole derivatives. The reaction exhibited a broad substrate scope and good functional group tolerance under metal-free conditions, affording the desired products in moderate to good yields. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/31803894/Lewis_or_Brønsted_acid_catalysed_reaction_of_propargylic_alcohol_tethered_alkylidenecyclopropanes_with_indoles_and_pyrroles_for_the_preparation_of_polycyclic_compounds_tethered_with_indole_or_pyrrole_motif_ DB - PRIME DP - Unbound Medicine ER -
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