Intramolecular [2+3]-addition of an azide to a C=C double bond as a novel approach to piperazines

Tetrahedron Letters

Volumn 46, Issue 7, 2005, Pages 1205-1207

  Lukina, Tatjana V ^a   Sviridov, Sergey I ^b   Shorshnev, Sergey V ^b   Alexandrov, Grigory G ^b   Stepanov, Aleksandr E ^a  

^a MIREA RUSSIAN TECHNOLOGICAL UNIVERSITY   (Russian Federation)

^b ChemBridge Corporation   (Russian Federation)

Author keywords

1,2,3 Triazolines; Azides; Intramolecular cycloaddition; Piperazines

Indexed keywords

PIPERAZINE DERIVATIVE; PYRAZINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CRYSTAL STRUCTURE; CYCLOADDITION; POLYMERIZATION; PRECURSOR; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 12344256970     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.071     Document Type: Article

References (15)

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11. 2Ph), 40.81 (C-4), 46.42 (C-7), 52.44 (C-3a), 56.45 (C-6), 67.88 (C-3), 124.66, 130.95, 132.07, 133.74, 136.71, 147.42 (carbons of Ns), 126.88, 128.58, 129.47, 133.35 (Ph)
12. 2 (all data) = 0.1804. Supplementary data in the form of CIFs have been deposited with the Cambridge Crystallographic Data Centre (CCDC 249283 and 249284). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ]
13. 2 = H) can be isolated sometimes in ∼15% yield
14. 2 = Me; X = I) were isolated when an excess of methyl iodide was used. In other cases, no quaternization was observed
15. 2Ph)