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Metal-Free Oxidative Spirocyclization of Alkynes with Sulfonylhydrazides Leading to 3-Sulfonated Azaspiro[4,5]trienones.
J Org Chem. 2015 May 15; 80(10):4966-72.JO

Abstract

A novel and direct oxidative spirocyclization of arylpropiolamides with sulfonylhydrazides leading to 3-sulfonated azaspiro[4,5]trienones has been developed under metal-free conditions. The reaction is performed in a tandem manner constituted by the sequential sulfonylation of alkynes, ipso-carbocyclization, dearomatization, hydration, and oxidation processes, providing a convenient and efficient approach to various sulfonated azaspiro[4,5] trienones of biological importance.

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Authors+Show Affiliations

Wen J
The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, China.
Wei W
The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, China.
Xue S
The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, China.
Yang D
The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, China.
Lou Y
The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, China.
Gao C
The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, China.
Wang H
The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, China.

MeSH

AlkynesCyclizationHydrazinesMetalsMolecular StructureOxidation-ReductionSpiro CompoundsSulfhydryl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

25928832

Citation

Wen, Jiangwei, et al. "Metal-Free Oxidative Spirocyclization of Alkynes With Sulfonylhydrazides Leading to 3-Sulfonated Azaspiro[4,5]trienones." The Journal of Organic Chemistry, vol. 80, no. 10, 2015, pp. 4966-72.
Wen J, Wei W, Xue S, et al. Metal-Free Oxidative Spirocyclization of Alkynes with Sulfonylhydrazides Leading to 3-Sulfonated Azaspiro[4,5]trienones. J Org Chem. 2015;80(10):4966-72.
Wen, J., Wei, W., Xue, S., Yang, D., Lou, Y., Gao, C., & Wang, H. (2015). Metal-Free Oxidative Spirocyclization of Alkynes with Sulfonylhydrazides Leading to 3-Sulfonated Azaspiro[4,5]trienones. The Journal of Organic Chemistry, 80(10), 4966-72. https://doi.org/10.1021/acs.joc.5b00361
Wen J, et al. Metal-Free Oxidative Spirocyclization of Alkynes With Sulfonylhydrazides Leading to 3-Sulfonated Azaspiro[4,5]trienones. J Org Chem. 2015 May 15;80(10):4966-72. PubMed PMID: 25928832.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Metal-Free Oxidative Spirocyclization of Alkynes with Sulfonylhydrazides Leading to 3-Sulfonated Azaspiro[4,5]trienones. AU - Wen,Jiangwei, AU - Wei,Wei, AU - Xue,Shengnan, AU - Yang,Daoshan, AU - Lou,Yu, AU - Gao,Chaoyang, AU - Wang,Hua, Y1 - 2015/05/07/ PY - 2015/5/1/entrez PY - 2015/5/1/pubmed PY - 2015/12/31/medline SP - 4966 EP - 72 JF - The Journal of organic chemistry JO - J Org Chem VL - 80 IS - 10 N2 - A novel and direct oxidative spirocyclization of arylpropiolamides with sulfonylhydrazides leading to 3-sulfonated azaspiro[4,5]trienones has been developed under metal-free conditions. The reaction is performed in a tandem manner constituted by the sequential sulfonylation of alkynes, ipso-carbocyclization, dearomatization, hydration, and oxidation processes, providing a convenient and efficient approach to various sulfonated azaspiro[4,5] trienones of biological importance. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/25928832/Metal_Free_Oxidative_Spirocyclization_of_Alkynes_with_Sulfonylhydrazides_Leading_to_3_Sulfonated_Azaspiro[45]trienones_ DB - PRIME DP - Unbound Medicine ER -