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.

Autor:	Lenshmidt, L. V., Ledovskaya, M. S., Larina, A. G., Filatov, A. S., Molchanov, A. P., Kostikov, R. R., Stepakov, A. V.
Předmět:	ISOQUINOLINE synthesis INDOLE derivatives RING formation (Chemistry) HYDROXYL group ISOXAZOLES
Zdroj:	Russian Journal of Organic Chemistry; Jan2018, Vol. 54 Issue 1, p112-125, 14p, 13 Diagrams
Abstrakt:	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. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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