Russian Chemical Bulletin, volume 63, issue 2, pages 552-553

Synthesis of 4,8-dihydro-7H-[1,2]dithiolo[3,4-b][1,2,5]oxadiazolo-[3,4-e]pyrazine-7-thione as a new heterocyclic system

Publication typeJournal Article
Publication date2014-02-01
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor1.7
ISSN10665285, 15739171
General Chemistry
Abstract
Sulfur monochloride and its complexes with tertiary amines are important sources of sulfur in the synthesis of novel heterocyclic systems.1—4 This available and inex pensive reagent allows such transformations to be com pleted in one step.5 With 3,4 diaminofurazan and 4 ami no 3 nitrofurazan as examples, we have discovered an ear lier unknown transformation of the 1,2,5 oxadiazole ring into the 1,2,5 thiadiazole ring under the action of sulfur monochloride.6,7 By analyzing the results obtained, we concluded that the furazan ring should contain an NH substituent for this transformation to be successful. For a further study of reactions of 1,2,5 oxadiazoles with sulfur mono chloride, we used 3,4 bis(alkyl amino)furazans 1 (R = Et, Pri) as new starting materials. Earlier, we have found that the N ethyl8 and N isopropyl9 groups can also interact with S2Cl2, so the reaction pathway for com pounds 1 was unpredictable. It turned out that 3,4 bis(alkylamino)furazans 1 (R = Et (a), Pri (b)) both react with S2Cl2 in hot dimethyl formamide (100—105 C) over 2 h. The reaction with bis(ethylamino) derivative 1a gave an inseparable mixture of products, from which we failed to isolate individual compounds. The reaction with 3,4 bis(isopropylamino) furazan 1b yielded a product containing only one isopro pyl group (NMR data). Data from elemental analysis, 1H and 13C NMR spectroscopy, IR spectroscopy, and mass spectrometry suggest two possible tricyclic structures for this product: oxadiazolodithiolopyrazinethione 2 or thia diazolodithiolopyrazinone 3 (Scheme 1). X ray diffraction provided conclusive evidence for structure 2 (Fig. 1, Table 1). The formation of product 2 can be explained by a trans formation9,10 of the N isopropyl group of furazan 1b into R = Et (a), Pri (b)

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Multidisciplinary Digital Publishing Institute (MDPI)
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Konstantinova L. S. et al. Synthesis of 4,8-dihydro-7H-[1,2]dithiolo[3,4-b][1,2,5]oxadiazolo-[3,4-e]pyrazine-7-thione as a new heterocyclic system // Russian Chemical Bulletin. 2014. Vol. 63. No. 2. pp. 552-553.
GOST all authors (up to 50) Copy
Konstantinova L. S., KNYAZEVA E. A., Bagryanskaya I. Y., Obruchnikova N. V., Rakitin O. A. Synthesis of 4,8-dihydro-7H-[1,2]dithiolo[3,4-b][1,2,5]oxadiazolo-[3,4-e]pyrazine-7-thione as a new heterocyclic system // Russian Chemical Bulletin. 2014. Vol. 63. No. 2. pp. 552-553.
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TY - JOUR
DO - 10.1007/s11172-014-0469-y
UR - https://doi.org/10.1007%2Fs11172-014-0469-y
TI - Synthesis of 4,8-dihydro-7H-[1,2]dithiolo[3,4-b][1,2,5]oxadiazolo-[3,4-e]pyrazine-7-thione as a new heterocyclic system
T2 - Russian Chemical Bulletin
AU - KNYAZEVA, E. A.
AU - Bagryanskaya, I. Yu.
AU - Obruchnikova, N V
AU - Rakitin, O A
AU - Konstantinova, L S
PY - 2014
DA - 2014/02/01 00:00:00
PB - Springer Nature
SP - 552-553
IS - 2
VL - 63
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2014_Konstantinova
author = {E. A. KNYAZEVA and I. Yu. Bagryanskaya and N V Obruchnikova and O A Rakitin and L S Konstantinova},
title = {Synthesis of 4,8-dihydro-7H-[1,2]dithiolo[3,4-b][1,2,5]oxadiazolo-[3,4-e]pyrazine-7-thione as a new heterocyclic system},
journal = {Russian Chemical Bulletin},
year = {2014},
volume = {63},
publisher = {Springer Nature},
month = {feb},
url = {https://doi.org/10.1007%2Fs11172-014-0469-y},
number = {2},
pages = {552--553},
doi = {10.1007/s11172-014-0469-y}
}
MLA
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Konstantinova, L. S., et al. “Synthesis of 4,8-dihydro-7H-[1,2]dithiolo[3,4-b][1,2,5]oxadiazolo-[3,4-e]pyrazine-7-thione as a new heterocyclic system.” Russian Chemical Bulletin, vol. 63, no. 2, Feb. 2014, pp. 552-553. https://doi.org/10.1007%2Fs11172-014-0469-y.
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