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The Structure and Configuration of Novel Polycyclic Products Derived from an Alicyclic 1,5,9‐Trione and Binucleophiles
Author(s) -
Kravchenko Natalia S.,
Denisenko Vladimir A.,
Akimova Taisia I.
Publication year - 2009
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.200800444
Subject(s) - chemistry , alicyclic compound , hemiacetal , isomerization , diamine , ketone , stereochemistry , organic chemistry , catalysis
As a continuation of our research of reactions with alicyclic 1,5,9‐trione 1 and its polycyclic form 2 , we have studied their reactions with binucleophiles, e.g. , phenylene‐1,2‐diamine and 2‐aminophenol, leading to novel N,O‐containing polycyclic compounds. Trione 1 formed double cyclization products 11 and 12 with 2‐aminophenol and triple cyclization product 15 with phenylene‐1,2‐diamine. Hemiacetal 2 and its dehydration product 5 reacted with binucleophiles through initial isomerization into the intermediate cyclic form 4 of trione 1 . Thus, ketone 5 reacted with 2‐aminophenol stereoselectively unlike the hemiacetal 2 . The structure and configuration of the reaction products were studied by using advanced spectroscopic techniques including 1D‐ and 2D‐NMR experiments.