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Formation of 10/12/14‐Membered Rings is Favored over 5/6/7‐Membered. An Unexpected Result from Oxazole Chemistry
Author(s) -
Slobodyanyuk Evgeniy Y.,
Berezowska Yulia L.,
Solomin Vitaliy V.,
Volochnyuk Dmitriy M.,
Rozhenko Alexander B.,
Ryabukhin Sergey V.,
Grygorenko Oleksandr O.
Publication year - 2019
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.201900914
Subject(s) - chemistry , oxazole , ring (chemistry) , stereochemistry , base (topology) , medicinal chemistry , organic chemistry , mathematical analysis , mathematics
Base‐promoted cyclization of N ‐Boc ‐ω ‐(4‐(chloromethyl)oxazol‐5‐yl)alkylamines led to the corresponding “dimerization” products containing fused 10‐, 12‐, and 14‐membered rings. Experimental data showed that the formation of these ring systems is favored over the corresponding 5‐/6‐/7‐membered ones, which was partially confirmed by DFT calculations; this effect was especially significant in the case of the 5‐/10‐membered pair.