Synthesis of Isoxazolopyrrolo[2,1-a]isoquinoline, Isoxazolo[5′,4′: 1,2]indolizino[8,7-b]indole, and Isoxazolo-[5,4-a]thieno[2,3-g]indolizine Derivatives by Intramolecular Cyclization of Hydroxylactams Constituting a Fragment of the Pyrroloisoxazole System
- Autores: Lenshmidt L.V.1, Ledovskaya M.S.1, Larina A.G.1, Filatov A.S.1, Molchanov A.P.1, Kostikov R.R.1, Stepakov A.V.1,2
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Afiliações:
- St. Petersburg State University
- Voeikov Main Geophysical Observatory
- Edição: Volume 54, Nº 1 (2018)
- Páginas: 112-125
- Seção: Article
- URL: https://journal-vniispk.ru/1070-4280/article/view/217175
- DOI: https://doi.org/10.1134/S1070428018010116
- ID: 217175
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Resumo
6-Hydroxy-5-[2-(naphthalen-1-yl)ethyl]-3a,5,6,6a-tetrahydro-4H-pyrrolo[3,4-d]isoxazol-4-ones in the presence of boron trifluoride–diethyl ether complex underwent cyclization to benzo[f]isoxazolo[5′,4′: 3,4]- pyrrolo[2,1-a]isoquinoline derivatives as mixtures of two diastereoisomers. Analogous cyclization of 6-hydroxy- 5-(naphthalen-1-ylmethyl)-3a,5,6,6a-tetrahydro-4H-pyrrolo[3,4-d]isoxazol-4-ones gave benzo[de]isoxazolo[ 5′,4′: 3,4]pyrrolo[2,1-a]isoquinolines as a single diastereoisomer. The cyclization of 6-hydroxy-5-[2-(1Hindol- 3-yl)ethyl]-6,6a-dihydro-3aH-pyrrolo[3,4-d]isoxazol-4(5H)-ones catalyzed by Sn(NTf2)4 afforded isoxazolo[ 5′,4′: 1,2]indolizino[8,7-b]indol-4(12H)-ones in moderate yields. 6-Hydroxy-5-[2-(thiophen-2-yl)ethyl]-6,6a-dihydro-3aH-pyrrolo[3,4-d]isoxazol-4(5H)-ones were converted to 4,5,10a,10b-tetrahydroisoxazolo- [5,4-a]thieno[2,3-g]indolizin-7(7aH)-one derivatives in the presence of BF3 · Et2O or Sn(NTf2)4.
Sobre autores
L. Lenshmidt
St. Petersburg State University
Email: alstepakov@yandex.ru
Rússia, Universitetskaya nab. 7/9, St. Petersburg, 199034
M. Ledovskaya
St. Petersburg State University
Email: alstepakov@yandex.ru
Rússia, Universitetskaya nab. 7/9, St. Petersburg, 199034
A. Larina
St. Petersburg State University
Email: alstepakov@yandex.ru
Rússia, Universitetskaya nab. 7/9, St. Petersburg, 199034
A. Filatov
St. Petersburg State University
Email: alstepakov@yandex.ru
Rússia, Universitetskaya nab. 7/9, St. Petersburg, 199034
A. Molchanov
St. Petersburg State University
Email: alstepakov@yandex.ru
Rússia, Universitetskaya nab. 7/9, St. Petersburg, 199034
R. Kostikov
St. Petersburg State University
Email: alstepakov@yandex.ru
Rússia, Universitetskaya nab. 7/9, St. Petersburg, 199034
A. Stepakov
St. Petersburg State University; Voeikov Main Geophysical Observatory
Autor responsável pela correspondência
Email: alstepakov@yandex.ru
Rússia, Universitetskaya nab. 7/9, St. Petersburg, 199034; ul. Karbysheva 7, St. Petersburg, 194021
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