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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‐2 H ‐inden‐2‐ylidene)malononitrile
Author(s) -
Alizadeh Abdolali,
Sadeghi Vahideh,
Bayat Fahimeh,
Zhu LongGuan
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300459
Subject(s) - chemistry , isoquinoline , cycloaddition , malononitrile , acetylene , propyne , inert gas , 1,3 dipolar cycloaddition , indene , proton nmr , medicinal chemistry , tetrahydroisoquinoline , organic chemistry , catalysis
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 ).