Home / Publications / 1,3-Dipolar cycloadditions of nonstabilised azomethine ylides at 3-substituted coumarins: synthesis of 1-benzopyrano[3,4-c]pyrrolidines

1,3-Dipolar cycloadditions of nonstabilised azomethine ylides at 3-substituted coumarins: synthesis of 1-benzopyrano[3,4-c]pyrrolidines

, 
Vyacheslav Yakovlevich Sosnovskikh 1
Vyacheslav Yakovlevich Sosnovskikh
, 
Pavel Alexandrovich Slepukhin 2
Pavel Alexandrovich Slepukhin
, 
Gerd-Volker Roeschenthaler 3
Gerd-Volker Roeschenthaler
10.1016/j.mencom.2012.01.011
Published 2011-12-29
Communication , Volume 22, Issue 1, 29-31
23
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Moshkin V. S. et al. 1,3-Dipolar cycloadditions of nonstabilised azomethine ylides at 3-substituted coumarins: synthesis of 1-benzopyrano[3,4-c]pyrrolidines // Mendeleev Communications. 2011. Vol. 22. No. 1. pp. 29-31.
GOST all authors (up to 50) Copy
Moshkin V. S., Sosnovskikh V. Y., Slepukhin P. A., Roeschenthaler G. 1,3-Dipolar cycloadditions of nonstabilised azomethine ylides at 3-substituted coumarins: synthesis of 1-benzopyrano[3,4-c]pyrrolidines // Mendeleev Communications. 2011. Vol. 22. No. 1. pp. 29-31.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2012.01.011
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.01.011
TI - 1,3-Dipolar cycloadditions of nonstabilised azomethine ylides at 3-substituted coumarins: synthesis of 1-benzopyrano[3,4-c]pyrrolidines
T2 - Mendeleev Communications
AU - Moshkin, Vladimir Sergeevich
AU - Sosnovskikh, Vyacheslav Yakovlevich
AU - Slepukhin, Pavel Alexandrovich
AU - Roeschenthaler, Gerd-Volker
PY - 2011
DA - 2011/12/29
PB - Mendeleev Communications
SP - 29-31
IS - 1
VL - 22
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2011_Moshkin,
author = {Vladimir Sergeevich Moshkin and Vyacheslav Yakovlevich Sosnovskikh and Pavel Alexandrovich Slepukhin and Gerd-Volker Roeschenthaler},
title = {1,3-Dipolar cycloadditions of nonstabilised azomethine ylides at 3-substituted coumarins: synthesis of 1-benzopyrano[3,4-c]pyrrolidines},
journal = {Mendeleev Communications},
year = {2011},
volume = {22},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.01.011},
number = {1},
pages = {29--31},
doi = {10.1016/j.mencom.2012.01.011}
}
MLA
Cite this
MLA Copy
Moshkin, Vladimir Sergeevich, et al. “1,3-Dipolar cycloadditions of nonstabilised azomethine ylides at 3-substituted coumarins: synthesis of 1-benzopyrano[3,4-c]pyrrolidines.” Mendeleev Communications, vol. 22, no. 1, Dec. 2011, pp. 29-31. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.01.011.

Abstract

Reaction of 3-substituted coumarins with N-alkyl-α-amino acids and aldehydes proceeds regio- and stereoselectively to give 1-benzopyrano[3,4-c]pyrrolidines as a result of 1,3-dipolar cycloaddition of the intermediate azomethine ylides at the Δ3-bond of the coumarins.

References

2.
Recent Advances in Azomethine Ylide Chemistry
Tsuge O., Kanemasa S.
Advances in Heterocyclic Chemistry, 1989
4.
Azomethine Ylides in Organic Synthesis
Najera C., Sansano J.
Current Organic Chemistry, 2003
7.
Drugs related to tetrahydrocannabinol
Razdan R.K., Howes J.F.
Medicinal Research Reviews, 1983
8.
Synthesis of new 3,4-disubstituted pyrrolidines as thromboxane A2/prostaglandin H2 (TP) receptor antagonists
Dubuffet T., Muller O., Simonet S.S., Descombes J., Laubie M., Verbeuren T.J., Lavielle G.
Bioorganic and Medicinal Chemistry Letters, 1996
9.
Novel benzopyrano[3,4-c]pyrrole derivatives as potent and selective dopamine D3 receptor antagonist.
Dubuffet T., Newman-Tancredi A., Cussac D., Audinot V., Loutz A., Millan M.J., Lavielle G.
Bioorganic and Medicinal Chemistry Letters, 1999
10.
(c) G. Lavielle, T. Dubuffet, M. J. Millan and A. Newman-Tancredi, US Patent 5663191, 1997;
11.
(d) M. D. Meyer, R. J. Altenbach, F. Z. Basha, W. A. Carroll, I. Drizin, J. F. Kerwin, M. D. Wendt, A. R. Haight and W. Zhang, US Patent 6046207, 2000;
12.
Synthesis of hexahydro[2]benzopyrano[3,4-c]pyrroles as serotonin 5-HT2C receptor agonists via intramolecular hetero Diels–Alder reactions
Kiyoi T., Reid M., Francis S., Davies K., Laats S., McArthur D., Easson A., Kiyoi Y., Tarver G., Caulfield W., Gibson K., Wishart G., Morrison A.J., Adam J.M., Ray P., et. al.
Tetrahedron Letters, 2011
14.
Drugs derived from cannabinoids. 1. Nitrogen analogs, benzopyranopyridines and benzopyranopyrroles.
Pars H.G., Granchelli F.E., Razdan R.K., Keller J.K., Teiger D.G., Rosenberg F.J., Harris L.S.
Journal of Medicinal Chemistry, 1976
15.
A Scaleable Synthesis of Fiduxosin
Haight A.R., Bailey A.E., Baker W.S., Cain M.H., Copp R.R., DeMattei J.A., Ford K.L., Henry R.F., Hsu M.C., Keyes R.F., King S.A., McLaughlin M.A., Melcher L.M., Nadler W.R., Oliver P.A., et. al.
Organic Process Research and Development, 2004
17.
XY–ZH systems as potential 1,3-dipoles. Part 12. Mechanism of formation of azomethine ylides via the decarboxylative route from α-amino acids
Grigg R., Idle J., McMeekin P., Surendrakumar S., Vipond D.
Journal of the Chemical Society Perkin Transactions 1, 1988
21.
1,3-Dipolar cycloadditions of azomethine ylides with dipolarophiles. II. Synthesis of pyrrolizidines
Orsini F., Pelizzoni F., Forte M., Sisti M., Merati F., Gariboldi P.
Journal of Heterocyclic Chemistry, 1988
23.
A synthesis of 1-azabicyclo[2.2.1]heptane-3-carboxylic acid esters in enantiomerically pure form
Cottrell I.F., Hands D., Kennedy D.J., Paul K.J., Wright S.H., Hoogsteen K.
Journal of the Chemical Society Perkin Transactions 1, 1991
24.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007