Efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine
Efficient optimized method for the synthesis of 3-amino-5,6-diphenyl-1,2,4-triazine was developed.
Gespeichert in:
| Datum: | 2008 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | English |
| Veröffentlicht: |
Інститут молекулярної біології і генетики НАН України
2008
|
| Online Zugang: | https://nasplib.isofts.kiev.ua/handle/123456789/7334 |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| Назва журналу: | Digital Library of Periodicals of National Academy of Sciences of Ukraine |
| Zitieren: | Efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine / D.M. Musatov, D.V. Kurilov, A.K. Rakishev // Ukrainica Bioorganica Acta. — 2008. — Т. 6, № 1. — С. 61-62. — Бібліогр.: 6 назв. — англ. |
Institution
Digital Library of Periodicals of National Academy of Sciences of Ukraine| id |
nasplib_isofts_kiev_ua-123456789-7334 |
|---|---|
| record_format |
dspace |
| spelling |
nasplib_isofts_kiev_ua-123456789-73342025-02-09T20:47:19Z Efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine Ефективний синтез 3-амiно-5,6-дифенiл-1,2,4-триазину Musatov, D.M. Kurilov, D.V. Rakishev, A.K. Efficient optimized method for the synthesis of 3-amino-5,6-diphenyl-1,2,4-triazine was developed. Розроблено ефективний та оптимальний підхід до синтезу 3-аміно-5,6-дифеніл-1,2,4-триазину. 2008 Article Efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine / D.M. Musatov, D.V. Kurilov, A.K. Rakishev // Ukrainica Bioorganica Acta. — 2008. — Т. 6, № 1. — С. 61-62. — Бібліогр.: 6 назв. — англ. 1814-9758 https://nasplib.isofts.kiev.ua/handle/123456789/7334 en application/pdf Інститут молекулярної біології і генетики НАН України |
| institution |
Digital Library of Periodicals of National Academy of Sciences of Ukraine |
| collection |
DSpace DC |
| language |
English |
| description |
Efficient optimized method for the synthesis of 3-amino-5,6-diphenyl-1,2,4-triazine was developed. |
| format |
Article |
| author |
Musatov, D.M. Kurilov, D.V. Rakishev, A.K. |
| spellingShingle |
Musatov, D.M. Kurilov, D.V. Rakishev, A.K. Efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine |
| author_facet |
Musatov, D.M. Kurilov, D.V. Rakishev, A.K. |
| author_sort |
Musatov, D.M. |
| title |
Efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine |
| title_short |
Efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine |
| title_full |
Efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine |
| title_fullStr |
Efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine |
| title_full_unstemmed |
Efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine |
| title_sort |
efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine |
| publisher |
Інститут молекулярної біології і генетики НАН України |
| publishDate |
2008 |
| url |
https://nasplib.isofts.kiev.ua/handle/123456789/7334 |
| citation_txt |
Efficient synthesis of 3-amino-5,6-diphenyl-l,2,4-triazine / D.M. Musatov, D.V. Kurilov, A.K. Rakishev // Ukrainica Bioorganica Acta. — 2008. — Т. 6, № 1. — С. 61-62. — Бібліогр.: 6 назв. — англ. |
| work_keys_str_mv |
AT musatovdm efficientsynthesisof3amino56diphenyll24triazine AT kurilovdv efficientsynthesisof3amino56diphenyll24triazine AT rakishevak efficientsynthesisof3amino56diphenyll24triazine AT musatovdm efektivniisintez3amino56difenil124triazinu AT kurilovdv efektivniisintez3amino56difenil124triazinu AT rakishevak efektivniisintez3amino56difenil124triazinu |
| first_indexed |
2025-11-30T15:54:45Z |
| last_indexed |
2025-11-30T15:54:45Z |
| _version_ |
1850231317933850624 |
| fulltext |
61
Introduction. The derivatives of 1,2,4�tri�
azines are of interest as physiologically active
compounds. In particular the 3�amino�5,6�
diphenyl�1,2,4�triazine (3) shows antimalarial
activity [1] and represents key intermediate for
the synthesis of 2,3,6�tri�replaced imidazo[1,2�
b]�1,2,4�triazines and replaced 6�hydroxy�8H�
pyrimido[1,2�b]�1,2,4�triazin�8�ones possessing
potential antineoplastic activity [2]. Besides,
among the derivatives of imidazo — [1,2�b]�
1,2,4�triazines obtained from triazine 3 com�
pounds with an intensive luminescence are
found out, which also are capable of generating
in soutions and vapor the laser radiation in visi�
ble range of a spectrum.
The synthesis of 3�amino�5,6�diphenyl�1,2,4�
triazine (3) by means of the condensation of
dibenzoyl and semicarbazide at the further
reaction of obtained 3�hydroxy�5,6�diphenyl�
1,2,4�triazine with POCl3 followed by the pro�
cessing of 3�chloro�5,6�diphenyl�1,2,4�triazine
with a solution of ammonia appears labour�con�
suming enough and demands severe conditions
for realization of last stage, during which
replacement of atom of chlorine on amino group
in 6�th position was carried out under pressure
at temperature of 140 °C.
More simple and efficient method of the syn�
thesis of 3�amino�5,6�diphenyl�1,2,4�triazine (3)
appears as a condensation of dibenzoyl (1) with
aminoguanidine bicaronate (2). We carried out
the synthesis of triazine 3 (scheme 1) at refluxing
of initial components in n�BuOH followed by a
washing of a precipitate with a mix of Et2O�hexa�
ne (1:1). The yield of product has reached 97 %.
It is necessary to note that in examples
known from the literature sources for a case
when the triazine 3 obtained at refluxing initial
components in EtOH [5, 6] or benzene [1] tech�
niques of the synthesis have not been optimized
and the yield of the required product made up
not more than 30�60 %.
The structure of obtained triazine 3 is proved
by data of 1H, 13C NMR� and mass�spectroscopy.
Experimental section. Melting point was
measured on a device «Boetius». Spectra NMR
were registered on a spectrometer «Bruker AM�
300» (300 MHz). Mass�spectrum was registered
on a mass�spectrometer «Kratos MS�30» (elec�
tron ionization, 70 eV, direct inlet, source tem�
perature 200 °C).
33[[AAmmiinnoo[[55,,66[[ddiipphheennyyll[[11,,22,,44[[ttrriiaazziinnee ((33)).. Add
13.61 g (0.1 mol) aminoguanidine bicaronate (2)
to a solution 21.02 g (0.1 mol) of dibenzoyl (1) in
50 ml of n�BuOH at intensive stirring.
Further a reaction mixture heat at refluxing
for 6 hours, cool up to a room temperature and
maintain within 24 hours at 5 °C before end of
crystallization. An obtained precipitate dry up
Efficient synthesis of 3�amino�5,6�diphenyl�1,2,4�triazine
D.M. Musatov, D.V. Kurilov*, A.K. Rakishev
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
47 Leninsky prosp., Moscow, 119991, Russian Federation
Summary. Efficient optimized method for the synthesis of 3�amino�5,6�diphenyl�1,2,4�triazine was
developed.
Keywords: 3�amino�5,6�diphenyl�1,2,4�triazine, dibenzoyl, aminoguanidine bicaronate.
Ukrainica Bioorganica Acta 1 (2008) 61—62
www.bioorganica.org.ua
* Corresponding author.
Tel.: +7499�1355306
E�mail address: kur�dv@mail.ru
© Д.М. Мусатов, Д.В. Курiлов, О.К. Ракiшев, 2008
D.M. Musatov, D.V. Kurilov, A.K. Rakishev
62 Ukrainica Bioorganica Acta 1 (2008)
and wash out by 100 ml of a mixture Et2O�hexa�
ne (1:1). After drying in vacuum the yield of
product 3 has made up 24.05 g (97 %).
M.p. 174.5�175.5 °C (lit.: 175 °C [5]).
1H NMR spectrum (DMSO�d6, δ): 7.23 (br s,
2H, NH2), 7.31�7.37 (m, 7H, Arom), 7.39�7.44 (m,
3H, Arom).
13C NMR spectrum (DMSO�d6, δ): 127.7, 127.9,
128.9, 129.2, 129.8, 136.2, 136.5, 148.6, 156.1, 161.7.
Mass spectrum, m/z (Irel, %): 248 (M+·, 26), 220
(0.5), 178 (100), 165 (5), 152 (6), 126 (2), 103 (10),
76 (23), 59 (11), 43 (18).
Надійшла в редакцію 10.10.2007 р.
O
O
Ph
Ph
+
NH
NHNH2H2N H2CO3
n-BuOH
reflux, 6h
N
N
NPh
Ph NH2
1 2 3
Scheme 1
Synthesis of 3[amino[5,6[diphenyl[1,2,4[triazine
References
Ефективний синтез 3�амiно�5,6�дифенiл�1,2,4�триазину
Д.М. Мусатов, Д.В. Курiлов, О.К. Ракiшев
Iнститут органiчної хiмiї iм. M.Д. Зелiнського РАН
Ленiнський пр�т, 47, Москва, 119991, Росiйська Федерацiя
Резюме. Розроблено ефективний та оптимальний пiдхiд до синтезу 3�амiно�5,6�дифенiл�1,2,4�триазину.
Ключовi слова: 3�амiно�5,6�дифенiл�1,2,4�триaзин, дибензоїл, амiногуанiдин бiкарбонат.
1. March L.C., Bajwa G.S., Lee J., Wasti Kh., Joul[
liJ M.M. Antimalarials. 3. 1,2,4�Triazines // J. Med.
Chem. — 1976. — Vol. 19, No. 6. — P. 845�848.
2. Labouta I.M., Soliman F.S.G., Kassem M.G. Some sub�
stituted imidazo[1,2�b][1,2,4]�triazines and 8H�pyrimido[1,2�
b][1,2,4]triazine�8�ones as potential antineoplastic agents
// Pharmazie. — 1986. — Vol. 41, No. 11. — P. 812�813.
3. Кругленко В.П., Повстяной М.В., Клюев Н.А.
Конденсированные имидазо�1,2,4�азины. 9. Производ�
ные имидазо[1,2�b]�1,2,4�триазина в реакциях элект�
рофильного замещения // Химия гетероцикл. соеди�
нений. — 1984. — № 3. — С. 413�416.
4. Laakso P.V., Robinson R., Vandrewala H.P. Studies
in the triazine series including a new synthesis of 1,2,4�
triazines // Tetrahedron. — 1957. — Vol. 1, No. 1�2. —
P. 103�118.
5. Thiele J., Bihan R. Condensationsproducte des
Amidoguanidins mit aromatischen Aldehyden und Ke�
tonen // Justus Liebigs Ann. Chem. — 1898. — Bd. 302.
— S. 299�311.
6. Elvidge J.A., Newbold G.T., Senciall I.R., Symes T.G.
Aminophenyl�1,2,4�triazines and analogues and their
orientation by proton magnetic resonance spectroscopy
// J. Chem. Soc. — 1964. — P. 4157�4162.
|