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

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The first example of the stereoselective synthesis and crystal structure of a spirobicycloquinazolinone based on (-)-fenchone and anthranilamide. / Chernyshov, Vladimir V.; Gatilov, Yuri V.; Yarovaya, Olga I. et al.

In: Acta Crystallographica Section C: Structural Chemistry, Vol. 75, 01.12.2019, p. 1675-1680.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{9ba67c8044b345fd8e098cc2e1251acd,

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

abstract = "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-1′H-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 1H and 13C 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){\AA}. The formation of dimers via N - H⋯O=C hydrogen bonds with an interaction energy of 93.30kJmol-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.",

keywords = "crystal structure, intermolecular interactions, l-fenchone, porosity, quinazolinone, spirocyclic compound, ASYMMETRIC-SYNTHESIS, ACID, SET, ANALOGS, NATURAL-PRODUCTS, L-fenchone, CYCLOADDITION, CONSTRUCTION, QUINAZOLINONE, ENANTIOSELECTIVE TOTAL-SYNTHESIS, DERIVATIVES",

author = "Chernyshov, {Vladimir V.} and Gatilov, {Yuri V.} and Yarovaya, {Olga I.} and Koskin, {Igor P.} and Yarovoy, {Spartak S.} and Brylev, {Konstantin A.} and Salakhutdinov, {Nariman F.}",

year = "2019",

month = dec,

day = "1",

doi = "10.1107/S2053229619015766",

language = "English",

volume = "75",

pages = "1675--1680",

journal = "Acta Crystallographica Section C: Structural Chemistry",

issn = "2053-2296",

publisher = "John Wiley and Sons Inc.",

}

RIS

TY - JOUR

T1 - The first example of the stereoselective synthesis and crystal structure of a spirobicycloquinazolinone based on (-)-fenchone and anthranilamide

AU - Chernyshov, Vladimir V.

AU - Gatilov, Yuri V.

AU - Yarovaya, Olga I.

AU - Koskin, Igor P.

AU - Yarovoy, Spartak S.

AU - Brylev, Konstantin A.

AU - Salakhutdinov, Nariman F.

PY - 2019/12/1

Y1 - 2019/12/1

N2 - 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-1′H-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 1H and 13C 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)Å. The formation of dimers via N - H⋯O=C hydrogen bonds with an interaction energy of 93.30kJmol-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.

AB - 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-1′H-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 1H and 13C 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)Å. The formation of dimers via N - H⋯O=C hydrogen bonds with an interaction energy of 93.30kJmol-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.

KW - crystal structure

KW - intermolecular interactions

KW - l-fenchone

KW - porosity

KW - quinazolinone

KW - spirocyclic compound

KW - ASYMMETRIC-SYNTHESIS

KW - ACID

KW - SET

KW - ANALOGS

KW - NATURAL-PRODUCTS

KW - L-fenchone

KW - CYCLOADDITION

KW - CONSTRUCTION

KW - QUINAZOLINONE

KW - ENANTIOSELECTIVE TOTAL-SYNTHESIS

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85076151851&partnerID=8YFLogxK

U2 - 10.1107/S2053229619015766

DO - 10.1107/S2053229619015766

M3 - Article

C2 - 31802758

AN - SCOPUS:85076151851

VL - 75

SP - 1675

EP - 1680

JO - Acta Crystallographica Section C: Structural Chemistry

JF - Acta Crystallographica Section C: Structural Chemistry

SN - 2053-2296

ER -

ID: 22848535