Abstract
The title compound, C19H18N2O4, a rare example of a spirocyclic orthoamide, was synthesized by a double cyclization of a N-Boc protected sarcosine derivative. The crystal structure of the racemic (R,R/S,S) modification reveals two near-orthogonal five-membered heterocyclic ring systems, each in an envelope configuration.
Highlights
The title compound, C19H18N2O4, a rare example of a spirocyclic orthoamide, was synthesized by a double cyclization of a N-Boc protected sarcosine derivative
We have recently reported (Nazarian & Forsyth, 2016) the preparation of 1,6-dioxa-3,9-diazaspiro[4,4]nonane-2,8-diones, a new class of spirocyclic othoamide. These were achieved by double cyclization of O-acylated hydroxamides utilizing a modification of an analogous procedure for 2-oxy-1,3-oxazolidin-4-ones (Kamimura et al, 2002, 2003, 2006)
The crystal packing of molecules of B1 reveals a weak intermolecular offset – ring interaction between parallel, inversion-related, phenyl rings [Cg1Á Á ÁCg1i 4.608 (1) A, offset 3.196 A, interplanar separation ca 3.32 A, Cg1 defined by atoms C7–C12; symmetry code: (i) Àx, Ày, Àz]
Summary
The biological significance of spirocyclic molecules has inspired considerable research towards the discovery of new synthetic routes to such compounds (Rios, 2012). We have recently reported (Nazarian & Forsyth, 2016) the preparation of 1,6-dioxa-3,9-diazaspiro[4,4]nonane-2,8-diones, a new class of spirocyclic othoamide. These were achieved by double cyclization of O-acylated hydroxamides utilizing a modification of an analogous procedure for 2-oxy-1,3-oxazolidin-4-ones (Kamimura et al, 2002, 2003, 2006). The structure comprises two approximately orthogonal five-membered heterocyclic ring systems [angle between least squares planes = 87.12 (5)].
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
