Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Short Paper | Regular issue | Vol 98, No. 1, 2019, pp.88-95
Published online, 24th January, 2019
DOI: 10.3987/COM-18-14006
Reaction of 2,3,5,6,7,8-Hexahydroquinoxaline with Thiourea Derivatives: Analysis of the Structure and Conformational State of [4.4.3]Propellane

Kazuhide Nakahara,* Koki Yamaguchi, and Hisao Kansui

*Department of Integrative Pharmaceutical Sciences, Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan

Abstract

The reaction of 2,3,5,6,7,8-hexahydroquinoxaline with thiourea derivatives yields a propellane-type tetraazaindene structure, whose conformation was established by 2D NMR analysis and molecular orbital calculations, and verified by single-crystal X-ray diffraction analysis. Further, the result obtained from X-ray analysis of this propellane-type tetraazaindene structure indicated that the crystalline state was stabilized by specific hydrogen bonds; four hydrogen bonds were of the type >C=S•••H–N, four of N–H•••N type between the imidazolidine moieties, and two of >C=S•••H–C type.