Synthesis of tetrahydrochromenes and dihydronaphthofurans via a cascade process of [3 + 3] and [3 + 2] annulation reactions: mechanistic insight for 6- endo-trig and 5- exo-trig cyclisation

Yeruva Pavankumar Reddy; V Srinivasadesikan; Rengarajan Balamurugan; M C Lin; Shaik Anwar

doi:10.1039/d2ra08163f

Synthesis of tetrahydrochromenes and dihydronaphthofurans via a cascade process of [3 + 3] and [3 + 2] annulation reactions: mechanistic insight for 6- endo-trig and 5- exo-trig cyclisation

RSC Adv. 2023 Feb 16;13(9):5796-5803. doi: 10.1039/d2ra08163f. eCollection 2023 Feb 14.

Authors

Yeruva Pavankumar Reddy¹, V Srinivasadesikan¹, Rengarajan Balamurugan², M C Lin³, Shaik Anwar¹

Affiliations

¹ Department of Chemistry, School of Applied Sciences and Humanities, Vignan's Foundation for Science Technology and Research-VFSTR (Deemed to be University) Vadlamudi-522213 Guntur Andhra Pradesh India [email protected] [email protected] https://www.vignan.ac.in/bshanwar.php +91-8632344700.
² School of Chemistry, University of Hyderabad Gachibowli Hyderabad India 500046.
³ Department of Applied Chemistry, National Yang Ming Chiao Tung University Hsinchu 30010 Taiwan.

Abstract

Substituted tetrahydrochromenes and dihydronaphthofurans are easily accessible by the treatment of β-tetralone with trans-β-nitro styrene derived Morita-Baylis-Hillman (MBH) acetates through a formal [3 + 3]/[3 + 2] annulation. The reaction proceeds through a cascade Michael/oxa-Michael pathway with moderate to good yields. A DFT study was carried out to account for the formation of the corresponding six and five-membered heterocycles via 6-endo-trig and 5-exo-trig cyclization.