TY - JOUR

T1 - Synthesis of isoxazolopyrrolo[2,1-a]isoquinoline, isoxazolo[5',4'

T2 - 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

AU - Lenshmidt, L. V.

AU - Ledovskaya, M. S.

AU - Larina, A. G.

AU - Filatov, A. S.

AU - Molchanov, A. P.

AU - Kostikov, R. R.

AU - Stepakov, A. V.

N1 - Funding Information: This study was performed under financial support by the Russian Foundation for Basic Research (project no. 16-33-00792) using the equipment of the Magnetic Resonance Research Center, Center for X-Ray Diffraction Studies, Chemical Analysis and Materials Research Center, and Chemistry Educational Center of the St. Petersburg State University. Publisher Copyright: © Pleiades Publishing, Ltd., 2018. and L.V. Lenshmidt, M.S. Ledovskaya, A.G. Larina, A.S. Filatov, A.P. Molchanov, R.R. Kostikov, A.V. Stepakov, 2018. Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 2018

Y1 - 2018

N2 - 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.

AB - 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.

KW - 1,3-DIPOLAR CYCLOADDITION

KW - ACYLIMINIUM ION CYCLIZATION

KW - ALKALOID (+/-)-CRISPINE-A

KW - INHIBITORS

KW - ISOQUINOLINE ALKALOIDS

KW - ISOXAZOLOPYRROLOISOQUINOLINES

KW - LAMELLARIN ALKALOIDS

KW - PORTULACA-OLERACEA

KW - SKELETON

KW - TOPOISOMERASE-I

UR - http://www.scopus.com/inward/record.url?scp=85043771145&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/synthesis-isoxazolopyrrolo-2-1-isoquinoline-cyclization-hydroxylactams-constituting-fragment-pyrrolo

U2 - 10.1134/S1070428018010116

DO - 10.1134/S1070428018010116

M3 - Article

AN - SCOPUS:85043771145

VL - 54

SP - 112

EP - 125

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 1

ER -