Unusual tandem sequence of oxa Diels–Alder reaction, retro Diels–Alder reaction, and oxa 6π-electrocyclic ring opening in the reaction of 6-amino-4-(4-methoxyphenyl)-2H-pyran-2-ones with benzaldehydes

Adil I. Khatri; Shriniwas D. Samant

doi:10.1039/C4RA13374A

Unusual tandem sequence of oxa Diels–Alder reaction, retro Diels–Alder reaction, and oxa 6π-electrocyclic ring opening in the reaction of 6-amino-4-(4-methoxyphenyl)-2H-pyran-2-ones with benzaldehydes

Adil I. Khatri^a and Shriniwas D. Samant*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Institute of Chemical Technology, N. M. Parekh Road, Matunga, India
E-mail: sd.samant@ictmumbai.edu.in
Fax: +91 22 2269 2102
Tel: +91 22 3361 2606

Abstract

The oxa Diels–Alder reaction of 6-amino-4-(4-methoxyphenyl)-2H-pyran-2-ones with benzaldehydes took an unusual path whereby a tandem sequence of the oxa Diels–Alder reaction, retro Diels–Alder reaction, and 6π-electrocyclic ring opening of the pyran yielded 3-(4-methoxyphenyl)-5-phenyl-1-(piperidin-1-yl/pyrrolidin-1-yl)penta-2,4-dien-1-ones. The reaction took place in boiling toluene with a series of substituted benzaldehydes. An electron-donating group on benzaldehyde retarded the reaction, while an electron-withdrawing group favoured it, thus indicating the normal electron demand pathway.

Supplementary files

Publication details

The article was received on 29 Oct 2014, accepted on 21 Nov 2014 and first published on 21 Nov 2014

Article type: Communication

DOI: 10.1039/C4RA13374A

Author version available: Download Author version (PDF)

Citation: RSC Adv., 2015,5, 2009-2012

Request permissions
Unusual tandem sequence of oxa Diels–Alder reaction, retro Diels–Alder reaction, and oxa 6π-electrocyclic ring opening in the reaction of 6-amino-4-(4-methoxyphenyl)-2H-pyran-2-ones with benzaldehydes

A. I. Khatri and S. D. Samant, RSC Adv., 2015, 5, 2009
DOI: 10.1039/C4RA13374A
If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using RightsLink. Go to our Instructions for using RightsLink page for details.

Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.

For reproduction of material from PCCP:
Reproduced from Ref. XX with permission from the PCCP Owner Societies.

For reproduction of material from PPS:
Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.

For reproduction of material from all other RSC journals and books:
Reproduced from Ref. XX with permission from The Royal Society of Chemistry.
If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

In all cases the Ref. XX is the XXth reference in the list of references.

If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC

For reproduction of material from PCCP:
[Original citation] - Reproduced by permission of the PCCP Owner Societies

For reproduction of material from PPS:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC

For reproduction of material from all other RSC journals:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry
If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

RSC Advances

Unusual tandem sequence of oxa Diels–Alder reaction, retro Diels–Alder reaction, and oxa 6π-electrocyclic ring opening in the reaction of 6-amino-4-(4-methoxyphenyl)-2H-pyran-2-ones with benzaldehydes

Abstract

Supplementary files

Publication details

Unusual tandem sequence of oxa Diels–Alder reaction, retro Diels–Alder reaction, and oxa 6π-electrocyclic ring opening in the reaction of 6-amino-4-(4-methoxyphenyl)-2H-pyran-2-ones with benzaldehydes

Search articles by author

Spotlight

Advertisements