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 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...

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Autores principales: Reddy, Yeruva Pavankumar, Srinivasadesikan, V., Balamurugan, Rengarajan, Lin, M. C., Anwar, Shaik
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9932637/
https://www.ncbi.nlm.nih.gov/pubmed/36816068
http://dx.doi.org/10.1039/d2ra08163f
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author Reddy, Yeruva Pavankumar
Srinivasadesikan, V.
Balamurugan, Rengarajan
Lin, M. C.
Anwar, Shaik
author_facet Reddy, Yeruva Pavankumar
Srinivasadesikan, V.
Balamurugan, Rengarajan
Lin, M. C.
Anwar, Shaik
author_sort Reddy, Yeruva Pavankumar
collection PubMed
description 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.
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spelling pubmed-99326372023-02-17 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 Reddy, Yeruva Pavankumar Srinivasadesikan, V. Balamurugan, Rengarajan Lin, M. C. Anwar, Shaik RSC Adv Chemistry 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. The Royal Society of Chemistry 2023-02-16 /pmc/articles/PMC9932637/ /pubmed/36816068 http://dx.doi.org/10.1039/d2ra08163f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Reddy, Yeruva Pavankumar
Srinivasadesikan, V.
Balamurugan, Rengarajan
Lin, M. C.
Anwar, Shaik
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9932637/
https://www.ncbi.nlm.nih.gov/pubmed/36816068
http://dx.doi.org/10.1039/d2ra08163f
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