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Synthesis of unsubstituted 4H,8H-bisfurazano[3,4-b:3′,4′-e]pyrazine

Aleksei Borisovich Sheremetev 1
Aleksei Borisovich Sheremetev
, 
Igor L Yudin 1
Igor L Yudin
10.1070/MC1996v006n06ABEH000746
Published 1996-12-31
Communication , Volume 6, Issue 6, 247-248
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Sheremetev A. B., Yudin I. L. Synthesis of unsubstituted 4H,8H-bisfurazano[3,4-b:3′,4′-e]pyrazine // Mendeleev Communications. 1996. Vol. 6. No. 6. pp. 247-248.
GOST all authors (up to 50) Copy
Sheremetev A. B., Yudin I. L. Synthesis of unsubstituted 4H,8H-bisfurazano[3,4-b:3′,4′-e]pyrazine // Mendeleev Communications. 1996. Vol. 6. No. 6. pp. 247-248.
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TY - JOUR
DO - 10.1070/MC1996v006n06ABEH000746
UR - https://mendcomm.colab.ws/publications/10.1070/MC1996v006n06ABEH000746
TI - Synthesis of unsubstituted 4H,8H-bisfurazano[3,4-b:3′,4′-e]pyrazine
T2 - Mendeleev Communications
AU - Sheremetev, Aleksei Borisovich
AU - Yudin, Igor L
PY - 1996
DA - 1996/12/31
PB - Mendeleev Communications
SP - 247-248
IS - 6
VL - 6
ER -
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@article{1996_Sheremetev,
author = {Aleksei Borisovich Sheremetev and Igor L Yudin},
title = {Synthesis of unsubstituted 4H,8H-bisfurazano[3,4-b:3′,4′-e]pyrazine},
journal = {Mendeleev Communications},
year = {1996},
volume = {6},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1996v006n06ABEH000746},
number = {6},
pages = {247--248},
doi = {10.1070/MC1996v006n06ABEH000746}
}
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Sheremetev, Aleksei Borisovich, and Igor L Yudin. “Synthesis of unsubstituted 4H,8H-bisfurazano[3,4-b:3′,4′-e]pyrazine.” Mendeleev Communications, vol. 6, no. 6, Dec. 1996, pp. 247-248. https://mendcomm.colab.ws/publications/10.1070/MC1996v006n06ABEH000746.

Abstract

The title compound 2a was synthesized by a four-step sequence starting from 4,5-dichlorofurazano[3,4-b]pyrazine 3; the key step being a one-pot transformation of tetrazolo sulfilimine 6 to 2a via an oxidation/tetrazole ring cleavage/nitrogen loss/ring-closure/ proton trapping procedure.

References

1.
A. B. Sheremetev, G. A. Karozo, O. A. Rakitin, T. S. Novikova, T. I. Godovikova and L. I. Khmel’nitskii, USSR Pat., 1 643 546, 1991 (Chem. Abstr., 1992, 116, 59 384v).
2.
Sheremetev A.B., Mantseva E.V., Aleksandrova N.S., Kuz’min V.S., Khmel’nitskii L.I.
Mendeleev Communications, 1995
3.
Synthesis of 4,8-disubstituted 4H,8H-bis[1,2,5]oxadiazolo[3,4-6:3′,4′-e]pyrazines
Fischer J.W., Nissan R.A., Lowe-Ma C.K.
Journal of Heterocyclic Chemistry, 1991
4.
A. B. Sheremetev, O. V. Kharitonova, I. L. Yudin, V. A. Myasnikov, T. S. Novikova, L. I. Khmelnitskii, O. P. Shitov and V. A. Tartakovskii, USSR Pat., 1752734, 1992 (Chem. Abstr., 1993, 119, 271 166).
5.
A mild convenient synthesis of heterocyclic triphenylphosphine imines
Rakitin O.A., Obruchnikova N.V., Khmelnitski L.I.
Phosphorus, Sulfur and Silicon and the Related Elements, 1993
6.
10.1070/MC1996v006n06ABEH000746_bib6
Khisamutdinov
Izv. Akad. Nauk, Ser. Khim., 1993
7.
10.1070/MC1996v006n06ABEH000746_bib7
Rakitin
Izv. Akad. Nauk SSSR, Ser. Khim., 1990
8.
A new benzofurazan synthesis
Boulton A.J., Ghosh P.B., Katritzky A.R.
Tetrahedron Letters, 1966
10.
While the paper was in the press another method of 2a synthesis had been published, see: I. B. Starchenkov and V. G. Andrianov, Khim. Geterotsikl. Soedin., 1996, 717 (in Russian).