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

被引：4

作者：

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
]}

机构：

[1] NN Vorozhtsov Novosibirsk Inst Organ Chem SB RAS, 9 Acad Lavrentiev Ave, Novosibirsk 630090, Russia

[2] Novosibirsk State Univ, Pirogova St 2, Novosibirsk 630090, Russia

[3] Nikolaey Inst Inorgan Chem SB RAS, 3 Acad Lavrentiev Ave, Novosibirsk 630090, Russia

来源：

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY | 2019年 / 75卷

关键词：

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

D O I：

10.1107/S2053229619015766

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：1675 / +

页数：15

共 41 条

[1] Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].