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The first example of the stereoselective synthesis and crystal structure of a spirobicycloquinazolinone based on (–)‐fenchone and anthranilamide
Author(s) -
Chernyshov Vladimir V.,
Gatilov Yuri V.,
Yarovaya Olga I.,
Koskin Igor P.,
Yarovoy Spartak S.,
Brylev Konstantin A.,
Salakhutdinov Nariman F.
Publication year - 2019
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229619015766
Subject(s) - stereoselectivity , stereochemistry , chemistry , organic chemistry , catalysis
The possibility of a single‐stage solvent‐free stereoselective synthesis of a spirocyclic compound from the natural bicyclic monoterpenoid (−)‐fenchone and anthranilamide has been shown for the first time. The molecular and crystal structure of (1 R ,2 S ,4 S )‐1,3,3‐trimethyl‐1′ H ‐spiro[bicyclo[2.2.1]heptane‐2,2′‐quinazolin]‐4′(3′ H )‐one, C 17 H 22 N 2 O, was established by X‐ray diffraction though the chirality was assumed via the known reactant connectivity and 1 H and 13 C NMR spectroscopy. It has shown that in the molecule, for steric reasons, there is an elongation of the Me 2 C—C(N)N bond to 1.603 (5) Å. The formation of dimers via N—H…O=C hydrogen bonds with an interaction energy of 93.30 kJ mol −1 and through cavities (33.7% of the unit‐cell volume) was established in the packing of the molecules. There are no π‐stacking interactions in the structure.