3-azabicyclo[3.3.1]nonane derivatives: IV. Synthesis of amino acids with 3-azabicyclo[3.3.1]nonane fragment

Authors
Shakhkel'dyan, IV Nikiforova, EG Grudtsyn, YD Atroshchenko, YM Borbulevich, OY Efremov, YA Gitis, SS Moiseev, DN Alifanova, EN Chudakov, PV Kovalevskii, AY
Citation
Iv. Shakhkel'Dyan et al., 3-azabicyclo[3.3.1]nonane derivatives: IV. Synthesis of amino acids with 3-azabicyclo[3.3.1]nonane fragment, RUSS J ORG, 37(4), 2001, pp. 583-591
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
10704280 → ACNP
Volume
37
Issue
4
Year of publication
2001
Pages
583 - 591
Database
ISI
SICI code
1070-4280(200104)37:4<583:3DISOA>2.0.ZU;2-B
Abstract
A series of 1.5-dinitro-3-azabicyclo[3.3.1]non-6-enes was prepared by reduc tion of 1-R-2,4- and 1-R-3,5-dinitrobenzenes with potassium borohydride fol lowed by Mannich reaction with formaldehyde and amino acids. The molecular structure of (6-bromo-1,5-dinitro-3-azabicyclo[3.3.1]non-6-en-3-yl)acetic a cid was studied by X-ray diffraction analysis. The mechanism of decompositi on under electron impact was determined for (7-methoxy-1,5-dinitro-3-azabic yclo[3.3.1]non-6-en-3-yl)acetic acid.