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Diastereoselective Synthesis of Isoindole‐Fused Diazacyclooctaindenones from Spirochromenes through Domino Reactions with Aliphatic 1,2‐Diamines
Author(s) -
Pathak Sudipta,
Pramanik Animesh
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300096
Subject(s) - isoindole , chemistry , ethylenediamine , tandem , domino , ring (chemistry) , cascade reaction , organic chemistry , medicinal chemistry , stereochemistry , catalysis , materials science , composite material
A diastereoselective synthesis of isoindole‐fused diazacyclooctaindenone derivatives has been accomplished through tandem ring‐opening and ring‐closing of spirochromene derivatives triggered by different aliphatic 1,2‐diamines. When ethanolic solutions of spirochromenes are refluxed with different aliphatic 1,2‐diamines such as 1,2‐ethylenediamine, (±)‐1,2‐propylenediamine and (±)‐ trans ‐1,2‐cyclohexanediamine, the isoindole‐fused eight‐membered heterocycles are formed in moderate to high yields within 5–15 min.