1,3-Dipolar cycloaddition of ethyl 2,3-pentadienoate with pyridinium dicyanomethylides: Regiospecific formation of ethyl 3-cyano-2-ethylindolizine-1-carboxylates and a novel formation of tricyclic compounds

Naoto Hayashi; Naoto Kawajiri; Takane Uchida; Kiyoshi Matsumoto

doi:10.3987/COM-05-S(K)70

1,3-Dipolar cycloaddition of ethyl 2,3-pentadienoate with pyridinium dicyanomethylides: Regiospecific formation of ethyl 3-cyano-2-ethylindolizine-1-carboxylates and a novel formation of tricyclic compounds

Naoto Hayashi^*, Naoto Kawajiri, Takane Uchida, Kiyoshi Matsumoto

^*Corresponding author for this work

Program of Chemistry

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

2 Scopus citations

Abstract

Pyridinium dicyanomethylides underwent site-and regioslective 1,3-dipolar cycloaddition with ethyl 2,3-pentadienoate to give ethyl 3-cyano-2-ethylindolizine-1-carboxylates in moderate yields. In two cases, a novel type of the tricyclc compounds, in addition to indolizines, were obtained whose structure was established by a single crystal X-Ray analysis. A plausible mechanism for its formation is also presented.

Original language	English
Pages (from-to)	175-179
Number of pages	5
Journal	Heterocycles
Volume	66
Issue number	1
DOIs	https://doi.org/10.3987/COM-05-S(K)70
State	Published - 2005/12/31

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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@article{6da44356d86f44a0824f499d0574899b,

title = "1,3-Dipolar cycloaddition of ethyl 2,3-pentadienoate with pyridinium dicyanomethylides: Regiospecific formation of ethyl 3-cyano-2-ethylindolizine-1-carboxylates and a novel formation of tricyclic compounds",

abstract = "Pyridinium dicyanomethylides underwent site-and regioslective 1,3-dipolar cycloaddition with ethyl 2,3-pentadienoate to give ethyl 3-cyano-2-ethylindolizine-1-carboxylates in moderate yields. In two cases, a novel type of the tricyclc compounds, in addition to indolizines, were obtained whose structure was established by a single crystal X-Ray analysis. A plausible mechanism for its formation is also presented.",

author = "Naoto Hayashi and Naoto Kawajiri and Takane Uchida and Kiyoshi Matsumoto",

year = "2005",

month = dec,

day = "31",

doi = "10.3987/COM-05-S(K)70",

language = "英語",

volume = "66",

pages = "175--179",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "1",

}

1,3-Dipolar cycloaddition of ethyl 2,3-pentadienoate with pyridinium dicyanomethylides: Regiospecific formation of ethyl 3-cyano-2-ethylindolizine-1-carboxylates and a novel formation of tricyclic compounds. / Hayashi, Naoto; Kawajiri, Naoto; Uchida, Takane et al.
In: Heterocycles, Vol. 66, No. 1, 31.12.2005, p. 175-179.

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

TY - JOUR

T1 - 1,3-Dipolar cycloaddition of ethyl 2,3-pentadienoate with pyridinium dicyanomethylides

T2 - Regiospecific formation of ethyl 3-cyano-2-ethylindolizine-1-carboxylates and a novel formation of tricyclic compounds

AU - Hayashi, Naoto

AU - Kawajiri, Naoto

AU - Uchida, Takane

AU - Matsumoto, Kiyoshi

PY - 2005/12/31

Y1 - 2005/12/31

N2 - Pyridinium dicyanomethylides underwent site-and regioslective 1,3-dipolar cycloaddition with ethyl 2,3-pentadienoate to give ethyl 3-cyano-2-ethylindolizine-1-carboxylates in moderate yields. In two cases, a novel type of the tricyclc compounds, in addition to indolizines, were obtained whose structure was established by a single crystal X-Ray analysis. A plausible mechanism for its formation is also presented.

AB - Pyridinium dicyanomethylides underwent site-and regioslective 1,3-dipolar cycloaddition with ethyl 2,3-pentadienoate to give ethyl 3-cyano-2-ethylindolizine-1-carboxylates in moderate yields. In two cases, a novel type of the tricyclc compounds, in addition to indolizines, were obtained whose structure was established by a single crystal X-Ray analysis. A plausible mechanism for its formation is also presented.

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U2 - 10.3987/COM-05-S(K)70

DO - 10.3987/COM-05-S(K)70

M3 - 学術論文

AN - SCOPUS:33646878307

SN - 0385-5414

VL - 66

SP - 175

EP - 179

JO - Heterocycles

JF - Heterocycles

IS - 1

ER -