Mechanism of the inverse-electron demand Diels-Alder reaction of 2-aminopyrroles with 1,3,5-triazines: detection of an intermediate and effect of added base and acid

Michael De Rosa; David Arnold

doi:10.1016/j.tetlet.2007.03.012

Mechanism of the inverse-electron demand Diels-Alder reaction of 2-aminopyrroles with 1,3,5-triazines: detection of an intermediate and effect of added base and acid

Michael De Rosa
, David Arnold

Penn State Brandywine

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

In base, a 2-aminopyrrole reacted with a 1,3,5-triazine to give a zwitterion (Meisenheimer complex). Acid promoted its conversion to the pyrrolo[2,3-d]pyrimidine. A cascade mechanism with reversible steps is proposed to explain why both a base and an acid are needed for the cycloaddition to occur.

Original language	English (US)
Pages (from-to)	2975-2977
Number of pages	3
Journal	Tetrahedron Letters
Volume	48
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2007.03.012
State	Published - Apr 23 2007

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.03.012

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title = "Mechanism of the inverse-electron demand Diels-Alder reaction of 2-aminopyrroles with 1,3,5-triazines: detection of an intermediate and effect of added base and acid",

abstract = "In base, a 2-aminopyrrole reacted with a 1,3,5-triazine to give a zwitterion (Meisenheimer complex). Acid promoted its conversion to the pyrrolo[2,3-d]pyrimidine. A cascade mechanism with reversible steps is proposed to explain why both a base and an acid are needed for the cycloaddition to occur.",

author = "\{De Rosa\}, Michael and David Arnold",

note = "Funding Information: This work was supported by a Grant (CHE-0110801) from the National Science Foundation. We thank Dr. J. Honovich (Drexel University) for mass spectra and Dr. Alan Benesi (Penn State) for 19 F NMR spectra. X-ray crystallography was supported by the NSF Grant CHE-0131112 and carried out by Dr. Hemant Yennawar (Penn State). ",

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doi = "10.1016/j.tetlet.2007.03.012",

language = "English (US)",

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pages = "2975--2977",

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T1 - Mechanism of the inverse-electron demand Diels-Alder reaction of 2-aminopyrroles with 1,3,5-triazines

T2 - detection of an intermediate and effect of added base and acid

AU - De Rosa, Michael

AU - Arnold, David

N1 - Funding Information: This work was supported by a Grant (CHE-0110801) from the National Science Foundation. We thank Dr. J. Honovich (Drexel University) for mass spectra and Dr. Alan Benesi (Penn State) for 19 F NMR spectra. X-ray crystallography was supported by the NSF Grant CHE-0131112 and carried out by Dr. Hemant Yennawar (Penn State).

PY - 2007/4/23

Y1 - 2007/4/23

N2 - In base, a 2-aminopyrrole reacted with a 1,3,5-triazine to give a zwitterion (Meisenheimer complex). Acid promoted its conversion to the pyrrolo[2,3-d]pyrimidine. A cascade mechanism with reversible steps is proposed to explain why both a base and an acid are needed for the cycloaddition to occur.

AB - In base, a 2-aminopyrrole reacted with a 1,3,5-triazine to give a zwitterion (Meisenheimer complex). Acid promoted its conversion to the pyrrolo[2,3-d]pyrimidine. A cascade mechanism with reversible steps is proposed to explain why both a base and an acid are needed for the cycloaddition to occur.

UR - https://www.scopus.com/pages/publications/33947601037

UR - https://www.scopus.com/pages/publications/33947601037#tab=citedBy

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DO - 10.1016/j.tetlet.2007.03.012

M3 - Article

AN - SCOPUS:33947601037

SN - 0040-4039

VL - 48

SP - 2975

EP - 2977

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

Mechanism of the inverse-electron demand Diels-Alder reaction of 2-aminopyrroles with 1,3,5-triazines: detection of an intermediate and effect of added base and acid

Abstract

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