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

Substituted tetrahydrochromenes and dihydronaphthofurans are easily accessible by the treatment of β-tetralone with -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 mode...

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Bibliographic Details
Published in:RSC advances 2023-02, Vol.13 (9), p.5796-5803
Main Authors: Reddy, Yeruva Pavankumar, Srinivasadesikan, V, Balamurugan, Rengarajan, Lin, M C, Anwar, Shaik
Format: Article
Language:English
Subjects:
Acetates
Chemical reactions
Chemistry
Organic chemistry
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Summary:Substituted tetrahydrochromenes and dihydronaphthofurans are easily accessible by the treatment of β-tetralone with -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 6- and 5- cyclization.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra08163f