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Rearrangement of 5’,6’,7’,8’-tetrahydro-1’H-spiro(cyclohexane-1,2’-quinazolin)-4’(3’H)-one during the Vilsmeier reaction

Victor Ivanovich Markov 1
Victor Ivanovich Markov
Oleg Konstantinovich Farat 1
Oleg Konstantinovich Farat
Svetlana Anatol'evna Varenichenko 1
Svetlana Anatol'evna Varenichenko
Ekaterina Vladimirovna Velikaya 1
Ekaterina Vladimirovna Velikaya
1 Ukrainian State University of Chemical Technology, Dnepropetrovsk, Ukraine
Published 2012-02-27
CommunicationVolume 22, Issue 2, 101-102
12
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Markov V. I. et al. Rearrangement of 5’,6’,7’,8’-tetrahydro-1’H-spiro(cyclohexane-1,2’-quinazolin)-4’(3’H)-one during the Vilsmeier reaction // Mendeleev Communications. 2012. Vol. 22. No. 2. pp. 101-102.
GOST all authors (up to 50) Copy
Markov V. I., Farat O. K., Varenichenko S. A., Velikaya E. V. Rearrangement of 5’,6’,7’,8’-tetrahydro-1’H-spiro(cyclohexane-1,2’-quinazolin)-4’(3’H)-one during the Vilsmeier reaction // Mendeleev Communications. 2012. Vol. 22. No. 2. pp. 101-102.
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TY - JOUR
DO - 10.1016/j.mencom.2012.03.017
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.03.017
TI - Rearrangement of 5’,6’,7’,8’-tetrahydro-1’H-spiro(cyclohexane-1,2’-quinazolin)-4’(3’H)-one during the Vilsmeier reaction
T2 - Mendeleev Communications
AU - Markov, Victor Ivanovich
AU - Farat, Oleg Konstantinovich
AU - Varenichenko, Svetlana Anatol'evna
AU - Velikaya, Ekaterina Vladimirovna
PY - 2012
DA - 2012/02/27
PB - Mendeleev Communications
SP - 101-102
IS - 2
VL - 22
ER -
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@article{2012_Markov,
author = {Victor Ivanovich Markov and Oleg Konstantinovich Farat and Svetlana Anatol'evna Varenichenko and Ekaterina Vladimirovna Velikaya},
title = {Rearrangement of 5’,6’,7’,8’-tetrahydro-1’H-spiro(cyclohexane-1,2’-quinazolin)-4’(3’H)-one during the Vilsmeier reaction},
journal = {Mendeleev Communications},
year = {2012},
volume = {22},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.03.017},
number = {2},
pages = {101--102},
doi = {10.1016/j.mencom.2012.03.017}
}
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Markov, Victor Ivanovich, et al. “Rearrangement of 5’,6’,7’,8’-tetrahydro-1’H-spiro(cyclohexane-1,2’-quinazolin)-4’(3’H)-one during the Vilsmeier reaction.” Mendeleev Communications, vol. 22, no. 2, Feb. 2012, pp. 101-102. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.03.017.

Abstract

Treatment of 5’,6’,7’,8’-tetrahydro-1’H-spiro(cyclohexane-1,2’-quinazolin)-4’ (3’H)-one with POCl3 and DMF gives a mixture of 1,2,3,4,5,6,7,8-octahydroacridine-4-carbonitrile and 4,5-diformyl-2,3,6,7,8,10-hexahydroacridine-8a(1H)-carbonitrile, both products resulting from cascade transformations of the primary Vilsmeier intermediates.

References

1.
Novel Condensation of Cyclohexanone with Urea
McKAY A.F., TARLTON E.J., PODESVA C.
Journal of Organic Chemistry, 1961
2.
The Reaction of Urea with Cyclic 1,3-Dicarbonyl and Other Active Hydrogen Compounds
3.
�ber das Tetrahydrospiro [cyclohexan-1,2?(1?H)-chinazolin]-4?(3?H)-on
4.
A. V. Upadysheva, N.D. Grigor’eva and A. P. Znamenskaya, Khim. Geterotsikl. Soedin., 1977, 1549.[Chem. Heterocycl. Compd. (Engl. Transl.), 1977, 13, 1240].
5.
A. V. Upadysheva, N.D. Grigor’eva, Yu. S. Ryabokobylko and A. P. Znamenskaya, Khim. Geterotsikl. Soedin., 1983, 107.[Chem. Heterocycl. Compd. (Engl. Transl.), 1983, 19, 95].
7.
Heterocyclenbildung mit Enaminen
Bischoff C., Schr�der E.
Journal für praktische Chemie, 1992
8.
A new type of diene condensation reaction
Povarov L.S., Mikhailov B.M.
Russian Chemical Bulletin, 1963
11.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007