The first synthesis and X-ray crystal structure of tetrahydropyrrolo[2,3-d]azocines

Tetrahedron Letters

Volumn 43, Issue 38, 2002, Pages 6767-6769

  Varlamov, Alexey V ^a   Borisova, Tatiana N ^a   Voskressensky, Leonid G ^a   Soklakova, Tatiana A ^a   Kulikova, Larisa N ^a   Chernyshev, Alexey I ^a   Alexandrov, Grigory G ^b  

^a PEOPLES FRIENDSHIP UNIVERSITY OF RUSSIA   (Russian Federation)

^b KURNAKOV INSTITUTE OF GENERAL AND INORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Azocine; Cleavage; Pyrrole; Ring expansion

Indexed keywords

ACETONITRILE; AZOCINE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; EVAPORATION; MICHAEL ADDITION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0037119749     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01520-4     Document Type: Article

References (15)

1. Bosch J., Mauleon D., Boncompte F., Ganados R. J. Heterocyclic Chem. 18:1981;263.
2. Hayakawa J., Kawakami K., Seto H., Furihata K. Tetrahedron Lett. 33:1992;2701.
3. For the pyrrole-containing alkaloid Rhazinilam and related compounds synthesis and biological activity evaluation, see for example: (a) Banwell, M.; Edwards, A.; Smith, J.; Hamel, E.; Verdier-Pinard, P. J. Chem. Soc., Perkin Trans. 1 2000, 1497; (b) Pascal, C.; Dubois, J.; Guenard, D.; Gueritte, F. J. Org. Chem. 1998, 63, 6414; (c) David, B.; Sevenet, T.; Morgat, M.; Guenard, G.; Moisand, A.; Tollon, Y.; Thoison, O.; Wright, M. Cell Mobil. Cytoskel. 1994, 28, 317.
4. For the pyrrole-containing alkaloid Rhazinilam and related compounds synthesis and biological activity evaluation, see for example: (a) Banwell, M.; Edwards, A.; Smith, J.; Hamel, E.; Verdier-Pinard, P. J. Chem. Soc., Perkin Trans. 1 2000, 1497; (b) Pascal, C.; Dubois, J.; Guenard, D.; Gueritte, F. J. Org. Chem. 1998, 63, 6414; (c) David, B.; Sevenet, T.; Morgat, M.; Guenard, G.; Moisand, A.; Tollon, Y.; Thoison, O.; Wright, M. Cell Mobil. Cytoskel. 1994, 28, 317.
5. For the pyrrole-containing alkaloid Rhazinilam and related compounds synthesis and biological activity evaluation, see for example: (a) Banwell, M.; Edwards, A.; Smith, J.; Hamel, E.; Verdier-Pinard, P. J. Chem. Soc., Perkin Trans. 1 2000, 1497; (b) Pascal, C.; Dubois, J.; Guenard, D.; Gueritte, F. J. Org. Chem. 1998, 63, 6414; (c) David, B.; Sevenet, T.; Morgat, M.; Guenard, G.; Moisand, A.; Tollon, Y.; Thoison, O.; Wright, M. Cell Mobil. Cytoskel. 1994, 28, 317.
6. Varlamov A.V., Borisova T.N., Voskressensky L.G., Nsabimana B., Chernyshev A.I. Heterocyclic Commun. 7:2001;461.
7. 3 solutions, at 25°C using a Bruker WM 400 NMR spectrometer operating at 400 and 100 MHz, respectively. Mass-spectra were obtained by the EI technique (Finnigan-MAT 95 XL engine). General synthetic protocol: To a solution of 1 mmol of the THPP derivative in 10 ml of acetonitrile, 1.2 mmol of DMAD was added. The reaction mixture was stirred for 4-6 h at room temperature (TLC monitoring). Acetonitrile was evaporated under reduced pressure. The resulting residue was purified by column chromatography using ethyl acetate/hexane 1:1 mixture as eluent. The first fraction provided the corresponding pyrrolo[2,3-d]azocine derivatives as crystalline substances, which were recrystallized from ethyl acetate/hexane mixture.
8. 5: calcd C, 53.73; H, 5.26; N, 6.96; found C, 53.88; H, 5.65; N, 6.90.
9. 4: calcd C, 62.82; H, 5.80; N, 14.65; found C, 62.85; H, 5.65; N, 14.43.
10. 5: calcd C, 58.67; H, 4.70; N, 6.22; found C, 58.39; H, 4.72; N, 6.31.
11. SMART (control) and SAINT (Integration) Software, Version 5.0 Bruker AXS Inc., Madison, WI, 1997.
12. Sheldrick, G. M. SHELXS, Program for Crystal Structure Solution, University of Göttingen: Germany, 1997.
13. Sheldrick, G. M. SHELXL, Program for Crystal Structure Refinement, University of Göttingen: Germany, 1997.
14. Borisova T.N., Stazharova I.A., Aliev A.E., Prostakov N.S., Varlamov A.V. Chem. Heterocyclic Compd. (Engl. Transl.). 27:1991;1105.
15. For the review on THPP synthesis, see: Varlamov A.V., Borisova T.N., Voskressensky L.G. Synthesis. 2:2002;155.