Synthetic Potential of Regio- and Stereoselective Ring Expansion Reactions of Six-Membered Carbo- and Heterocyclic Ring Systems: A Review

Noor, Rida; Zahoor, Ameer Fawad; Mansha, Asim; Khan, Samreen Gul; Haq, Atta Ul; Ahmad, Sajjad; Al-Hussain, Sami A.; Irfan, Ali; Zaki, Magdi E. A.

doi:10.3390/ijms24076692

Open AccessReview

Synthetic Potential of Regio- and Stereoselective Ring Expansion Reactions of Six-Membered Carbo- and Heterocyclic Ring Systems: A Review

by

Rida Noor

¹,

Ameer Fawad Zahoor

^1,*

,

Asim Mansha

¹,

Samreen Gul Khan

¹,

Atta Ul Haq

¹

,

Sajjad Ahmad

²,

Sami A. Al-Hussain

³,

Ali Irfan

¹

and

Magdi E. A. Zaki

^3,*

¹

Department of Chemistry, Government College, University Faisalabad, Faisalabad 38000, Pakistan

²

Department of Chemistry, University of Engineering and Technology Lahore, Faisalabad Campus, Faisalabad 38000, Pakistan

³

Department of Chemistry, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 11623, Saudi Arabia

^*

Authors to whom correspondence should be addressed.

Int. J. Mol. Sci. 2023, 24(7), 6692; https://doi.org/10.3390/ijms24076692

Submission received: 13 February 2023 / Revised: 8 March 2023 / Accepted: 11 March 2023 / Published: 3 April 2023

(This article belongs to the Special Issue New Chemo-, Regio- and Stereoselective Reactions and Methods in Organic Synthesis)

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Abstract

Ring expansion reactions fascinate synthetic chemists owing to their importance in synthesizing biologically active compounds and their efficacy in medicinal chemistry. The present review summarizes a number of synthetic methodologies, including stereoselective and regioselective pathways adopted by scientists, for framing medium- to large-size carbo- and heterocycles involving lactams, lactone, azepine and azulene derivatives via ring expansion of six-membered carbo- and heterocycles that have been reported from 2007–2022. Numerous rearrangement and cycloaddition reactions involving Tiffeneau–Demjanov rearrangement, Aza–Claisen rearrangement, Schmidt rearrangement, Beckmann rearrangement, etc., have been described in this regard.

Keywords: six-member rings; heterocyclic ring expansion; azepine; azulene; biological activities

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MDPI and ACS Style

Noor, R.; Zahoor, A.F.; Mansha, A.; Khan, S.G.; Haq, A.U.; Ahmad, S.; Al-Hussain, S.A.; Irfan, A.; Zaki, M.E.A. Synthetic Potential of Regio- and Stereoselective Ring Expansion Reactions of Six-Membered Carbo- and Heterocyclic Ring Systems: A Review. Int. J. Mol. Sci. 2023, 24, 6692. https://doi.org/10.3390/ijms24076692

AMA Style

Noor R, Zahoor AF, Mansha A, Khan SG, Haq AU, Ahmad S, Al-Hussain SA, Irfan A, Zaki MEA. Synthetic Potential of Regio- and Stereoselective Ring Expansion Reactions of Six-Membered Carbo- and Heterocyclic Ring Systems: A Review. International Journal of Molecular Sciences. 2023; 24(7):6692. https://doi.org/10.3390/ijms24076692

Chicago/Turabian Style

Noor, Rida, Ameer Fawad Zahoor, Asim Mansha, Samreen Gul Khan, Atta Ul Haq, Sajjad Ahmad, Sami A. Al-Hussain, Ali Irfan, and Magdi E. A. Zaki. 2023. "Synthetic Potential of Regio- and Stereoselective Ring Expansion Reactions of Six-Membered Carbo- and Heterocyclic Ring Systems: A Review" International Journal of Molecular Sciences 24, no. 7: 6692. https://doi.org/10.3390/ijms24076692

APA Style

Noor, R., Zahoor, A. F., Mansha, A., Khan, S. G., Haq, A. U., Ahmad, S., Al-Hussain, S. A., Irfan, A., & Zaki, M. E. A. (2023). Synthetic Potential of Regio- and Stereoselective Ring Expansion Reactions of Six-Membered Carbo- and Heterocyclic Ring Systems: A Review. International Journal of Molecular Sciences, 24(7), 6692. https://doi.org/10.3390/ijms24076692

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Synthetic Potential of Regio- and Stereoselective Ring Expansion Reactions of Six-Membered Carbo- and Heterocyclic Ring Systems: A Review

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