The first example of the stereoselective synthesis and crystal structure of a spirobicycloquinazolinone based on (-)-fenchone and anthranilamide

The first example of the stereoselective synthesis and crystal structure of a spirobicycloquinazolinone based on (-)-fenchone and anthranilamide Full article

Journal

Acta Crystallographica Section C: Structural Chemistry
ISSN: 2053-2296

Output data

Year: 2019, Volume: 75, Pages: 1675-+ Pages count : DOI: 10.1107/S2053229619015766

Tags

quinazolinone; intermolecular interactions; spirocyclic compound; crystal structure; L-fenchone; porosity

Authors

Chernyshov Vladimir V. ^1,2 , Gatilov Yuri, V ^1,2 , Yarovaya Olga, I ^1,2 , Koskin Igor P. ¹ , Yarovoy Spartak S. ³ , Brylev Konstantin A. ^2,3 , Salakhutdinov Nariman F. ¹

Affiliations

1	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem SB RAS, 9 Acad Lavrentiev Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova St 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Nikolaey Inst Inorgan Chem SB RAS, 3 Acad Lavrentiev Ave, Novosibirsk 630090, Russia

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 (1R,2S,4S)-1,3,3-trimethyl-10H-spiro[bicyclo[2.2.1]heptane-2,2'-quinazolin]-4'(3'H)-one, C17H22N2O, was established by X-ray diffraction though the chirality was assumed via the known reactant connectivity and H-1 and C-13 NMR spectroscopy. It has shown that in the molecule, for steric reasons, there is an elongation of the Me2C-C(N)N bond to 1.603 (5) A degrees. The formation of dimers via N-H center dot center dot center dot 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 pi-stacking interactions in the structure.

Chernyshov V.V. , Gatilov Y.V. , Yarovaya O.I. , Koskin I.P. , Yarovoy S.S. , Brylev K.A. , Salakhutdinov N.F.
The first example of the stereoselective synthesis and crystal structure of a spirobicycloquinazolinone based on (-)-fenchone and anthranilamide
Acta Crystallographica Section C: Structural Chemistry. 2019. V.75. P.1675-+. DOI: 10.1107/S2053229619015766 WOS Scopus РИНЦ

Published online:	Nov 26, 2019
Published print:	Dec 1, 2019

Web of science	WOS:000500965400014
Scopus	2-s2.0-85076151851
Elibrary	43216159
OpenAlex	W2989885527