A Three-Component One-Pot Synthesis of Functionalized 5,5-Dicyanocyclopenta-1,3-dienes from Arylidene­malononitriles, Activated Acetylenes, and KCN or KSCN

The reaction of dialkyl acetylenedicarboxylates with arylidenemalononitriles in the presence of KSCN in MeCN led to a mixture of dialkyl (3E)‐4‐aryl‐3‐(arylideneamino)‐5,5‐dicyanocyclopenta‐1,3‐diene‐1,2‐dicarboxylates and dialkyl 4‐aryl‐5‐cyanothiophene‐2,3‐dicarboxylates. When these reactions were...

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Bibliographic Details
Published in:Helvetica chimica acta 2010-11, Vol.93 (11), p.2176-2182
Main Authors: Yavari, Issa, Sirouspour, Mehdi, Souri, Sanaz
Format: Article
Language:English
Subjects:
3-diene
4-aryl-5
4-aryl-5-cyano
5-dicyano
Acetylenic esters
arylidene
Cyanate
Cyclopenta-1
Cyclopenta‐1,3‐diene, 4‐aryl‐5,5‐dicyano
Malononitrile
Malononitrile, arylidene
Multicomponent reactions
Thiocyanate
Thiophene
Thiophene, 4‐aryl‐5‐cyano
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Summary:The reaction of dialkyl acetylenedicarboxylates with arylidenemalononitriles in the presence of KSCN in MeCN led to a mixture of dialkyl (3E)‐4‐aryl‐3‐(arylideneamino)‐5,5‐dicyanocyclopenta‐1,3‐diene‐1,2‐dicarboxylates and dialkyl 4‐aryl‐5‐cyanothiophene‐2,3‐dicarboxylates. When these reactions were performed in the presence of KCN, only the functionalized 5,5‐dicyanocyclopenta‐1,3‐dienes were obtained.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201000082