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Stereochemistry of 1,3‐dipolar‐cycloaddition of 3,4‐dihydroisoquinoline‐ and 3,4‐dihydro‐carboline‐ N ‐methoxycarbonyl‐ and N ‐phenacyl‐methylides with maleic and fumaric nitrile
Author(s) -
Kádas István,
Szántó Gábor,
Tőke László,
Simon AndrÁS,
Tóth Gábor
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440621
Subject(s) - chemistry , nitrile , yield (engineering) , stereoselectivity , cycloaddition , phenacyl , 1,3 dipolar cycloaddition , indole test , fumaric acid , stereochemistry , organic chemistry , materials science , metallurgy , catalysis
The 1,3‐dipolar‐cycloadditions of two kind of isoquinolinium and carbolinium ylides with fumaric and maleic nitrile resulted in pyrroloisoquinoline and indolizino[8,7‐ b ]indole derivatives, respectively, which are analogues of biologically active alkaloids. The cycloadditions were performed in good yield and proved to be stereoselective. The structure elucidation and complete 1 H and 13 C assignments have been achieved by a combination of various one‐ and two‐dimensional NMR experiments.