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Formation of cyclopropa[c]indole system in the Mn-mediated radical addition of cyclohexane-1,3-diones to N-substituted acrylamides

Mehmet Yilmaz 1
Mehmet Yilmaz
, 
Sedanur Birincioglu 1
Sedanur Birincioglu
, 
Ustalar Inal 1
Ustalar Inal
10.1016/j.mencom.2020.11.032
Published 2020-11-03
Communication , Volume 30, Issue 6, 785-787
4
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Yilmaz M., Birincioglu S., Inal U. Formation of cyclopropa[c]indole system in the Mn-mediated radical addition of cyclohexane-1,3-diones to N-substituted acrylamides // Mendeleev Communications. 2020. Vol. 30. No. 6. pp. 785-787.
GOST all authors (up to 50) Copy
Yilmaz M., Birincioglu S., Inal U. Formation of cyclopropa[c]indole system in the Mn-mediated radical addition of cyclohexane-1,3-diones to N-substituted acrylamides // Mendeleev Communications. 2020. Vol. 30. No. 6. pp. 785-787.
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TY - JOUR
DO - 10.1016/j.mencom.2020.11.032
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.11.032
TI - Formation of cyclopropa[c]indole system in the Mn-mediated radical addition of cyclohexane-1,3-diones to N-substituted acrylamides
T2 - Mendeleev Communications
AU - Yilmaz, Mehmet
AU - Birincioglu, Sedanur
AU - Inal, Ustalar
PY - 2020
DA - 2020/11/03
PB - Mendeleev Communications
SP - 785-787
IS - 6
VL - 30
ER -
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@article{2020_Yilmaz,
author = {Mehmet Yilmaz and Sedanur Birincioglu and Ustalar Inal},
title = {Formation of cyclopropa[c]indole system in the Mn-mediated radical addition of cyclohexane-1,3-diones to N-substituted acrylamides},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.11.032},
number = {6},
pages = {785--787},
doi = {10.1016/j.mencom.2020.11.032}
}
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Yilmaz, Mehmet, et al. “Formation of cyclopropa[c]indole system in the Mn-mediated radical addition of cyclohexane-1,3-diones to N-substituted acrylamides.” Mendeleev Communications, vol. 30, no. 6, Nov. 2020, pp. 785-787. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.11.032.

Keywords

benzofuran-2-carboxamides
carboxamides
cyclopropa[c]indoles
dihydrofurans
manganese(III) acetate
radical addition

Abstract

Manganese(III) acetate-mediated radical cyclization of N-substituted acrylamides with cyclohexane-1,3-diones gives 4-oxo-2,3,4,5,6,7-hexahydrobenzofuran-2-carboxamides and unexpected tricyclic 1,1a,5,6-tetrahydro-2H-cyclopropa[c]indole-2,7(3H)-diones. The structure of one representative tricyclic compound was confirmed by X-ray analysis. The reaction mechanism was examined employing some structural analogues of the reactants.

References

16.
Homologation of Protected Hexoses with Grignard C1 Reagents
Kim M., Grzeszczyk B., Zamojski A.
Tetrahedron, 2000
19.
Cyclization reactions of methylthioacetanilides
Liao Y., Wu Y., Chuang C.
Tetrahedron, 2003
27.
USTALAR A., YILMAZ M., OSMANİ A., KEÇELİ S.A.
Turkish Journal of Chemistry, 2017
34.
10.1016/j.mencom.2020.11.032_sbref0030a
Yilmaz
Turk. J. Chem., 2005
37.
Synthesis of Thienyl-Substituted Dihydrofuran Compounds Promoted by Manganese(III) Acetate
Biçer E., Yılmaz M., Burgaz E.V., Pekel A.T.
Helvetica Chimica Acta, 2013
40.
10.1016/j.mencom.2020.11.032_sbref0035b
Yilmaz
Turk. J. Chem., 2008
47.
Synthesis of dihydrofuro- and C-alkenylated naphthoquinones catalyzed by manganese(III) acetate
Alagöz O., Yılmaz M., Pekel A.T., Graiff C., Maggi R.
RSC Advances, 2014
55.
10.1016/j.mencom.2020.11.032_bib0070
Yilmaz
ARKIVOC, 2016
57.
Total synthesis of (±)-cycloclavine and (±)-5-epi-cycloclavine.
Petronijevic F.R., Wipf P.
Journal of the American Chemical Society, 2011
58.
Eight-Step Enantioselective Total Synthesis of (−)-Cycloclavine
McCabe S.R., Wipf P.
Angewandte Chemie - International Edition, 2016
60.
B. Ucan, PhD Thesis, 2005.