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Metal- and Base-Free Radical Cascade Cyclization/Hydrolysis of CN-Containing 1,6-Enynes with Ethers to Access Polyheterocycles.
Chem Asian J. 2023 Feb 01; 18(3):e202201149.CA

Abstract

A convenient and straightforward approach for the radical cascade cyclization/hydrolysis of CN-containing 1,6-enynes with simple ethers under metal- and base-free conditions is described. This strategy provides a variety of valuable ethers-substituted polyheterocycles via the construction of three C-C bonds, one C=O bond, and two new six-membered rings within a single procedure. The resulting products can smoothly undergo follow-up conversions to various useful scaffolds. The methodology shows excellent functional group tolerance, high step- and atom- economy, and mild reaction conditions, which can be further scaled up to gram quantity in a satisfactory yield.

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Publisher Full Text (DOI)

Authors+Show Affiliations

School of Materials Science and Chemical Engineering, Ningbo University, 315211, Ningbo, Zhejiang, P. R. China.

School of Materials Science and Chemical Engineering, Ningbo University, 315211, Ningbo, Zhejiang, P. R. China.

School of Materials Science and Chemical Engineering, Ningbo University, 315211, Ningbo, Zhejiang, P. R. China.

School of Materials Science and Chemical Engineering, Ningbo University, 315211, Ningbo, Zhejiang, P. R. China.

School of Materials Science and Chemical Engineering, Ningbo University, 315211, Ningbo, Zhejiang, P. R. China.

School of Materials Science and Chemical Engineering, Ningbo University, 315211, Ningbo, Zhejiang, P. R. China.

College of Chemistry and Materials Engineering, Wenzhou University, 325035, Wenzhou, P. R. China.

School of Materials Science and Chemical Engineering, Ningbo University, 315211, Ningbo, Zhejiang, P. R. China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

36550634

Citation

Zheng, Yan-Nan, et al. "Metal- and Base-Free Radical Cascade Cyclization/Hydrolysis of CN-Containing 1,6-Enynes With Ethers to Access Polyheterocycles." Chemistry, an Asian Journal, vol. 18, no. 3, 2023, pp. e202201149.

Zheng YN, Cai XE, Wu HL, et al. Metal- and Base-Free Radical Cascade Cyclization/Hydrolysis of CN-Containing 1,6-Enynes with Ethers to Access Polyheterocycles. Chem Asian J. 2023;18(3):e202201149.

Zheng, Y. N., Cai, X. E., Wu, H. L., Zhou, Y., Tian, W. C., Ruan, Y., Liu, H., & Wei, W. T. (2023). Metal- and Base-Free Radical Cascade Cyclization/Hydrolysis of CN-Containing 1,6-Enynes with Ethers to Access Polyheterocycles. Chemistry, an Asian Journal, 18(3), e202201149. https://doi.org/10.1002/asia.202201149

Zheng YN, et al. Metal- and Base-Free Radical Cascade Cyclization/Hydrolysis of CN-Containing 1,6-Enynes With Ethers to Access Polyheterocycles. Chem Asian J. 2023 Feb 1;18(3):e202201149. PubMed PMID: 36550634.

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

TY - JOUR T1 - Metal- and Base-Free Radical Cascade Cyclization/Hydrolysis of CN-Containing 1,6-Enynes with Ethers to Access Polyheterocycles. AU - Zheng,Yan-Nan, AU - Cai,Xue-Er, AU - Wu,Hong-Li, AU - Zhou,Yu, AU - Tian,Wen-Chan, AU - Ruan,Yiping, AU - Liu,Hongxin, AU - Wei,Wen-Ting, Y1 - 2023/01/10/ PY - 2022/12/21/revised PY - 2022/11/14/received PY - 2022/12/24/pubmed PY - 2022/12/24/medline PY - 2022/12/23/entrez KW - Base-free KW - CN-containing 1,6-enynes KW - cascade cyclization KW - green synthesis KW - metal-free SP - e202201149 EP - e202201149 JF - Chemistry, an Asian journal JO - Chem Asian J VL - 18 IS - 3 N2 - A convenient and straightforward approach for the radical cascade cyclization/hydrolysis of CN-containing 1,6-enynes with simple ethers under metal- and base-free conditions is described. This strategy provides a variety of valuable ethers-substituted polyheterocycles via the construction of three C-C bonds, one C=O bond, and two new six-membered rings within a single procedure. The resulting products can smoothly undergo follow-up conversions to various useful scaffolds. The methodology shows excellent functional group tolerance, high step- and atom- economy, and mild reaction conditions, which can be further scaled up to gram quantity in a satisfactory yield. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/36550634/Metal__and_Base_Free_Radical_Cascade_Cyclization/Hydrolysis_of_CN_Containing_16_Enynes_with_Ethers_to_Access_Polyheterocycles_ DB - PRIME DP - Unbound Medicine ER -