Synthesis of 1,2,3,6-Tetrahydropyridines via Aminophosphate Enabled Anionic Cascade and Acid Catalyzed Cyclization Approaches

Pradipta Das; Jon T. Njardarson

doi:10.1021/acs.orglett.5b01937

Synthesis of 1,2,3,6-Tetrahydropyridines via Aminophosphate Enabled Anionic Cascade and Acid Catalyzed Cyclization Approaches

Pradipta Das
, Jon T. Njardarson

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

14 Scopus citations

Abstract

Two new approaches for forming 1,2,3,6-tetrahydropyridines are reported. Both reactions employ a strategic phosphate substituent on the nitrogen atom. In the presence of an additional phosphate substituent (X = P = O(OEt)₂) an anionic cascade can by triggered upon treatment with base. Alternatively, when X = H the same 1,2,3,6-tetrahydropyridine product can be accessed via an acid catalyzed cyclization.

Original language	English (US)
Pages (from-to)	4030-4033
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.5b01937
State	Published - Aug 13 2015
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Two new approaches for forming 1,2,3,6-tetrahydropyridines are reported. Both reactions employ a strategic phosphate substituent on the nitrogen atom. In the presence of an additional phosphate substituent (X = P = O(OEt)2) an anionic cascade can by triggered upon treatment with base. Alternatively, when X = H the same 1,2,3,6-tetrahydropyridine product can be accessed via an acid catalyzed cyclization.",

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N2 - Two new approaches for forming 1,2,3,6-tetrahydropyridines are reported. Both reactions employ a strategic phosphate substituent on the nitrogen atom. In the presence of an additional phosphate substituent (X = P = O(OEt)2) an anionic cascade can by triggered upon treatment with base. Alternatively, when X = H the same 1,2,3,6-tetrahydropyridine product can be accessed via an acid catalyzed cyclization.

AB - Two new approaches for forming 1,2,3,6-tetrahydropyridines are reported. Both reactions employ a strategic phosphate substituent on the nitrogen atom. In the presence of an additional phosphate substituent (X = P = O(OEt)2) an anionic cascade can by triggered upon treatment with base. Alternatively, when X = H the same 1,2,3,6-tetrahydropyridine product can be accessed via an acid catalyzed cyclization.

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Synthesis of 1,2,3,6-Tetrahydropyridines via Aminophosphate Enabled Anionic Cascade and Acid Catalyzed Cyclization Approaches

Abstract

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