The intramolecular reaction of acetophenone N-tosylhydrazone and vinyl: Brønsted acid-promoted cationic cyclization toward polysubstituted indenes.
Chem Commun (Camb). 2021 Feb 19; 57(14):1810-1813.CC

Abstract

In the presence of TsNHNH2, a Brønsted acid-promoted intramolecular cyclization of o-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydic N-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, where N-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.

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Authors+Show Affiliations

Wang Z

School of Petrochemical Engineering, and Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, Changzhou University, Changzhou 213164, P. R. China.

Li Y

School of Petrochemical Engineering, and Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, Changzhou University, Changzhou 213164, P. R. China.

Chen F

Institute of New Materials & Industry Technology, College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. China. jiangcheng@cczu.edu.cn qpc@wzu.edu.cn.

Qian PC

Institute of New Materials & Industry Technology, College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. China. jiangcheng@cczu.edu.cn qpc@wzu.edu.cn.

Cheng J

School of Petrochemical Engineering, and Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, Changzhou University, Changzhou 213164, P. R. China and Institute of New Materials & Industry Technology, College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. China. jiangcheng@cczu.edu.cn qpc@wzu.edu.cn.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

33480891

Citation

Wang, Zhixin, et al. "The Intramolecular Reaction of Acetophenone N-tosylhydrazone and Vinyl: Brønsted Acid-promoted Cationic Cyclization Toward Polysubstituted Indenes." Chemical Communications (Cambridge, England), vol. 57, no. 14, 2021, pp. 1810-1813.

Wang Z, Li Y, Chen F, et al. The intramolecular reaction of acetophenone N-tosylhydrazone and vinyl: Brønsted acid-promoted cationic cyclization toward polysubstituted indenes. Chem Commun (Camb). 2021;57(14):1810-1813.

Wang, Z., Li, Y., Chen, F., Qian, P. C., & Cheng, J. (2021). The intramolecular reaction of acetophenone N-tosylhydrazone and vinyl: Brønsted acid-promoted cationic cyclization toward polysubstituted indenes. Chemical Communications (Cambridge, England), 57(14), 1810-1813. https://doi.org/10.1039/d0cc07966a

Wang Z, et al. The Intramolecular Reaction of Acetophenone N-tosylhydrazone and Vinyl: Brønsted Acid-promoted Cationic Cyclization Toward Polysubstituted Indenes. Chem Commun (Camb). 2021 Feb 19;57(14):1810-1813. PubMed PMID: 33480891.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - The intramolecular reaction of acetophenone N-tosylhydrazone and vinyl: Brønsted acid-promoted cationic cyclization toward polysubstituted indenes. AU - Wang,Zhixin, AU - Li,Yang, AU - Chen,Fan, AU - Qian,Peng-Cheng, AU - Cheng,Jiang, PY - 2021/1/23/pubmed PY - 2021/1/23/medline PY - 2021/1/22/entrez SP - 1810 EP - 1813 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 57 IS - 14 N2 - In the presence of TsNHNH2, a Brønsted acid-promoted intramolecular cyclization of o-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydic N-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, where N-tosylhydrazone served as an electrophile and alkylation reagent during this transformation. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/33480891/The_intramolecular_reaction_of_acetophenone_N_tosylhydrazone_and_vinyl:_Brønsted_acid_promoted_cationic_cyclization_toward_polysubstituted_indenes_ DB - PRIME DP - Unbound Medicine ER -

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The intramolecular reaction of acetophenone N-tosylhydrazone and vinyl: Brønsted acid-promoted cationic cyclization toward polysubstituted indenes.Chem Commun (Camb). 2021 Feb 19; 57(14):1810-1813.CC