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-Reference-Cited by-同舟云学术

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

Published:2023 Issue:9 Volume:13 Page:5796-5803
ISSN:2046-2069
Container-title:RSC Advances
language:en
Short-container-title:RSC Adv.

Author:

Reddy Yeruva Pavankumar¹,Srinivasadesikan V.¹,Balamurugan Rengarajan²^ORCID,Lin M. C.³,Anwar Shaik¹^ORCID

Affiliation:

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

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

A [3 + 3] and [3 + 2] annulation strategy using nitrostyrene derived MBH primary and secondary nitro allylic acetate for the construction of tetrahydrochromenes and dihydronaphthofurans at room temperature.

Funder

Science and Engineering Research Board

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemical Engineering,General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/RA/D2RA08163F

Reference63 articles.

1. Asymmetric α,γ-Regioselective [3 + 3] Formal Cycloadditions of α,β-Unsaturated Aldehydes via Cascade Dienamine–Dienamine Catalysis

2. Substrate-directed chemo- and regioselective synthesis of polyfunctionalized trifluoromethylarenes via organocatalytic benzannulation

3. Asymmetric synthesis of pyrano[2,3-c]pyrazoles via a cascade reaction between Morita–Baylis–Hillman acetates of nitroalkenes and pyrazolones

4. Base and catalyst-free synthesis of nitrobenzodiazepines via a cascade N-nitroallylation-intramolecular aza-Michael addition involving o-phenylenediamines and nitroallylic acetates

5. [3+2] regioselective annulation reaction of 2-arylidene-1,3-indandiones towards synthesis of spirocyclopentenes: understanding the mechanism of γ-attack vs. α-attack using DFT studies

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