An Approach to the Synthesis of Spiro[indene-pyridoisoquinoline] Derivatives via 1,4-Dipolar Cycloaddition of Isoquinoline and Acetylene Esters, and (1,3-Dihydro-1,3-dioxo-2H-inden-2-ylidene)malononitrile

A concise and efficient approach to the spiro‐tetrahydroisoquinoline derivatives has been developed by 1,4‐dipolar cycloaddition of zwitterions resulting from isoquinoline and acetylene esters and (1,3‐dihydro‐1,3‐dioxo‐2H‐inden‐2‐ylidene)malononitrile in MeCN at room temperature. The significance o...

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Published inHelvetica chimica acta Vol. 97; no. 10; pp. 1383 - 1387
Main Authors Alizadeh, Abdolali, Sadeghi, Vahideh, Bayat, Fahimeh, Zhu, Long-Guan
Format Journal Article
LanguageEnglish
Published Zürich WILEY-VCH Verlag 01.10.2014
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ISSN0018-019X
1522-2675
DOI10.1002/hlca.201300459

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Abstract A concise and efficient approach to the spiro‐tetrahydroisoquinoline derivatives has been developed by 1,4‐dipolar cycloaddition of zwitterions resulting from isoquinoline and acetylene esters and (1,3‐dihydro‐1,3‐dioxo‐2H‐inden‐2‐ylidene)malononitrile in MeCN at room temperature. The significance of this method lies in good yields and ease of product purification, and no inert atmosphere is required. The structures of the products were confirmed spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme).
AbstractList A concise and efficient approach to the spiro‐tetrahydroisoquinoline derivatives has been developed by 1,4‐dipolar cycloaddition of zwitterions resulting from isoquinoline and acetylene esters and (1,3‐dihydro‐1,3‐dioxo‐2 H ‐inden‐2‐ylidene)malononitrile in MeCN at room temperature. The significance of this method lies in good yields and ease of product purification, and no inert atmosphere is required. The structures of the products were confirmed spectroscopically (IR, 1 H‐ and 13 C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this reaction is proposed ( Scheme ).
A concise and efficient approach to the spiro‐tetrahydroisoquinoline derivatives has been developed by 1,4‐dipolar cycloaddition of zwitterions resulting from isoquinoline and acetylene esters and (1,3‐dihydro‐1,3‐dioxo‐2H‐inden‐2‐ylidene)malononitrile in MeCN at room temperature. The significance of this method lies in good yields and ease of product purification, and no inert atmosphere is required. The structures of the products were confirmed spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme).
A concise and efficient approach to the spiro-tetrahydroisoquinoline derivatives has been developed by 1,4-dipolar cycloaddition of zwitterions resulting from isoquinoline and acetylene esters and (1,3-dihydro-1,3-dioxo-2H-inden-2-ylidene)malononitrile in MeCN at room temperature. The significance of this method lies in good yields and ease of product purification, and no inert atmosphere is required. The structures of the products were confirmed spectroscopically (IR, H-1- and C-13-NMR, and EI-MS) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme).
Author Zhu, Long-Guan
Alizadeh, Abdolali
Sadeghi, Vahideh
Bayat, Fahimeh
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  organization: Department of Chemistry, Zhejiang University, Hangzhou 310027, P.R. China
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Issue 10
Keywords Propanedinitrile
Acetylene esters
ACID
Cycloadditions
DMAD ZWITTERION
Spiro-tetrahydroisoquinoline
ISOCYANIDES
Isoquinoline
3-dioxo-2H-inden-2-ylidene
2-
3-dihydro-1
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Snippet A concise and efficient approach to the spiro‐tetrahydroisoquinoline derivatives has been developed by 1,4‐dipolar cycloaddition of zwitterions resulting from...
A concise and efficient approach to the spiro-tetrahydroisoquinoline derivatives has been developed by 1,4-dipolar cycloaddition of zwitterions resulting from...
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StartPage 1383
SubjectTerms 3-dihydro-1
3-dioxo-2H-inden-2-ylidene
Acetylene esters
Chemistry
Chemistry, Multidisciplinary
Cycloadditions
Esters
Isoquinoline
Physical Sciences
Propanedinitrile
Propanedinitrile, 2‐(1,3‐dihydro‐1,3‐dioxo‐2H‐inden‐2‐ylidene)
Science & Technology
Spiro-tetrahydroisoquinoline
Title An Approach to the Synthesis of Spiro[indene-pyridoisoquinoline] Derivatives via 1,4-Dipolar Cycloaddition of Isoquinoline and Acetylene Esters, and (1,3-Dihydro-1,3-dioxo-2H-inden-2-ylidene)malononitrile
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