Spirocyclic dihydropyridines by electrophile-induced dearomatizing cyclization of N-alkenyl pyridinecarboxamides

Jemma Senczyszyn; Heloise Brice; Jonathan Clayden

doi:10.1021/ol400571j

Spirocyclic dihydropyridines by electrophile-induced dearomatizing cyclization of N-alkenyl pyridinecarboxamides

Jemma Senczyszyn, Heloise Brice, Jonathan Clayden^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

22 Citations (Scopus)

Abstract

On treatment with acylating or sulfonylating agents, N-alkenyl pyridine carboxamides (N-pyridinecarbonyl enamines) undergo a dearomatizing cyclization initiated by pyridine acylation and followed by intramolecular trapping of the resulting pyridinium cation. The products are spirocyclic dihydropyridines which may be further elaborated to spirocyclic heterocycles with drug-like features.

Original language	English
Pages (from-to)	1922-1925
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	8
Early online date	3 Apr 2013
DOIs	https://doi.org/10.1021/ol400571j
Publication status	Published - 19 Apr 2013

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title = "Spirocyclic dihydropyridines by electrophile-induced dearomatizing cyclization of N-alkenyl pyridinecarboxamides",

abstract = "On treatment with acylating or sulfonylating agents, N-alkenyl pyridine carboxamides (N-pyridinecarbonyl enamines) undergo a dearomatizing cyclization initiated by pyridine acylation and followed by intramolecular trapping of the resulting pyridinium cation. The products are spirocyclic dihydropyridines which may be further elaborated to spirocyclic heterocycles with drug-like features.",

author = "Jemma Senczyszyn and Heloise Brice and Jonathan Clayden",

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doi = "10.1021/ol400571j",

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T1 - Spirocyclic dihydropyridines by electrophile-induced dearomatizing cyclization of N-alkenyl pyridinecarboxamides

AU - Senczyszyn, Jemma

AU - Brice, Heloise

AU - Clayden, Jonathan

PY - 2013/4/19

Y1 - 2013/4/19

N2 - On treatment with acylating or sulfonylating agents, N-alkenyl pyridine carboxamides (N-pyridinecarbonyl enamines) undergo a dearomatizing cyclization initiated by pyridine acylation and followed by intramolecular trapping of the resulting pyridinium cation. The products are spirocyclic dihydropyridines which may be further elaborated to spirocyclic heterocycles with drug-like features.

AB - On treatment with acylating or sulfonylating agents, N-alkenyl pyridine carboxamides (N-pyridinecarbonyl enamines) undergo a dearomatizing cyclization initiated by pyridine acylation and followed by intramolecular trapping of the resulting pyridinium cation. The products are spirocyclic dihydropyridines which may be further elaborated to spirocyclic heterocycles with drug-like features.

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U2 - 10.1021/ol400571j

DO - 10.1021/ol400571j

M3 - Article (Academic Journal)

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SN - 1523-7060

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EP - 1925

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Spirocyclic dihydropyridines by electrophile-induced dearomatizing cyclization of N-alkenyl pyridinecarboxamides

Abstract

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