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Anomalous Behaviour of cis-Bicyclo[3.3.0]octane-3,7-dione and Its Derivatives During Twofold Fischer Indole Cyclization Using Low-Melting Mixtures

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Title Anomalous Behaviour of cis-Bicyclo[3.3.0]octane-3,7-dione and Its Derivatives During Twofold Fischer Indole Cyclization Using Low-Melting Mixtures
 
Creator KOTHA, S
CHINNAM, AK
 
Subject Weiss-Cook condensation
Fischer indole cyclization
low-melting mixture
cis-bicyclo[3.3.0]octane-3,7-dione
heterocycles
ALPHA-DIAZO ESTERS
GENERAL-APPROACH
WEISS REACTION
POLYQUINENES
DODECAHEDRANE
HYDRAZONES
ROUTE
 
Description We have developed an efficient method for the synthesis of the pentaleno[2,1-b: 5,4-b'] diindole and pentaleno[2,1-b: 5,6-b'] diindole skeletons via twofold Fischer indole cyclization. In this new procedure, cis-bicyclo[3.3.0] octane-3,7-dione on treatment with 1-methyl-1-phenylhydrazine in the presence of a low-melting mixture of L-(+)-tartaric acid and N, N'-dimethylurea at 70 degrees C undergoes a twofold Fischer indole cyclization to deliver the unusual C-s-symmetrical product pentaleno[2,1-b: 5,6-b'] diindole, along with the expected C-2-symmetrical pentaleno[2,1-b: 5,4-b'] diindole product.
 
Publisher GEORG THIEME VERLAG KG
 
Date 2014-12-28T11:55:31Z
2014-12-28T11:55:31Z
2014
 
Type Article
 
Identifier SYNTHESIS-STUTTGART, 46(3)301-306
0039-7881
1437-210X
http://dx.doi.org/10.1055/s-0033-1340341
http://dspace.library.iitb.ac.in/jspui/handle/100/16413
 
Language English