Preparation and mass spectrometric analysis of 5,6- dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione and 1,1'- (1,2-dioxoethane-1,2-diyl)bis-1,2,3,4-tetrahydroquinoline
Keywords:
1,2,3,4-tetrahydroquinoline, oxalyl chloride, mass spectrometry, column chromatography, 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione, 1,1'-(1,2-dioxoethane-1,2-diyl)bis- 1,2,3,4-tetrahydroquinoline.
Abstract
According to thin layer chromatography (eluent - chloroform) found to that the reaction of 1,2,3,4-
tetrahydroquinoline hydrochloride with oxalyl chloride in refluxing toluene exhaustively occurs for 1.5 h.
The product of this interaction is a mixture of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione (Rf 0,52),
and 1,1'-(1,2-dioxoethane-1,2-diyl)bis-1,2,3,4-tetrahydroquinoline (Rf 0,38) at a ratio of 3: 1. Purification of
the reaction mixture and separating the obtained compounds was performed by column chromatography. The
optimal eluent for the separation of the individual products was a mixture of carbon tetrachloride: chloroform
in the ratio 3: 1, the transmission rate of 2 cm3 / min. Product structure uniquely proved by means of mass
spectrometry. Mass spectrometric investigation of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione,
showed that of two cycles - hydropyridine and pyrroledione less stable is the last one. Under electron impact
in the ion-radical 1,1'-(1,2-dioxoethane-1,2-diyl)bis-1,2,3,4-tetrahydroquinoline symmetrically breaks up the
C-C bond dioxoethane moiety. Thus obtained radical cation emits a neutral molecule of CO to form ion
tetrahydroquinoline having maximum intensity (100%).
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Tetrahydro-4-quinolinamines identified as
novel P2Y1 receptor antagonists, Bioorganic &
Medicinal Chem. Letters, 2008, No. 18, pp.
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Ohmizu H., Kashimura Sh. Electroorganic
chemistry reaction of iminium ion with
nucleophile: a versatile synthesis of
tetrahydroquinolines and julolidines, J. Am.
Chem. Soc., 1982, No. 104, pp. 5753-5757.
3. Perry N.B., Blunt J.W., Munro M.H.G.
Cytotoxic pigments from new zealand sponges
of the genus latrunculia : discorhabdins a, b and
c, Tetrahedron, 1988, No. 44, pp. 1727-1734.
4. Miyoshi M., Morisaki N., Tokiwa Y.,
Kobayashi H., Iwasaki S. et al. Facile reductive
rearrangement of dynemicin a to dynemicin H:
the direct evidence for the p-phenylene
diradical intermediate, Tetrahedron Lett,. 1991,
No. 32, pp. 6007-6010.
5. Wender P. A., Beckham S., Mohler D.L.
The intramolecular addition of silylated alkynes
to aldehydes: Methodology for the construction
of cyclic enediynes and its application to
dynemicin analogs, Tetrahedron Lett, 1995, No.
36, pp. 209-212.
6. Witherup K.M., Ransom R.W., Graham
A.C., Bernard A.M., Salvatore M.J. et al.
Martinelline and martinellic acid, novel Gprotein
linked receptor antagonists from the
tropical plant Martinella iquitosensis
(Bignoniaceae), J. Am. Chem. Soc., 1995, No.
117, pp. 6682-6685.
7. Gracheva I.N., Gridneva L.I., Tochilkin
A.I., Gorkin V.Z. Hydrazides and sulfonyl
hydrazides from the series of quinoline are
human serum amine oxidase inhibitors, Khim.-
Farm. Zh. 1988, No. 22, pp. 1336-1339.
8. Youssefyeh R.D., Magnien E., Lee T.D.Y.,
Chan W.K., Lin C.J. et al. Development of a
novel series of (2-quinolinylmethoxy)phenylcontaining
compounds as high-affinity
leukotriene receptor antagonists. 1. Initial
structure-activity relationships, J. Med. Chem.,
1990, No. 33, pp. 1186-1194.
9. Pooley Ch.L., Edwards J.P., Goldman
M.E., Wang M-W, Marschke K.B et al.
Discovery and Preliminary SAR Studies of a
Novel, Nonsteroidal Progesterone Receptor
Antagonist Pharmacophore, J. Med. Chem.,
1998, No. 41, pp. 3461-3466.
10. El Tahir K.E.H., Al-Kharji A.M.H., Ageel
A.M. Effect of praziquantel and oxamniquine
on prostacyclin synthesis by the rat arterial and
myometrial tissues, Gen. Pharmac, 1992, No.
23, pp. 131-139.
11. Omura S., Nakagawa A. Structure of
virantmycin, a novel antiviral antibiotic ,
Tetrahedron Lett., 1981, No. 22, pp. 2199-2202.
12. Williamson N.M., March D.R., Ward
A.D. An improved synthesis of 2,2-
disubstituted-1,2-dihyroquinolines and their
conversion to 3-chloro-2,2-disubstitutedtetrahydroquinolines
, Tetrahedron Lett., 1995,
No. 36, pp. 7721-7724.
13. Kasaikina O.T., Kartasheva Z.S.,
Lobanova T.V. Osobennosti ingibirovaniya
okisleniya uglevodorodov gidrirovannymi khinolinami, Neftekhimiya. 1982, T. 22, No 2,
pp. 265-271.
14. Kasaikina O.T., Lobanova T.V., Fentsov
D.V. Mekhanizm ingibirovaniya protsessov
okisleniya uglevodorodov 2,2,4-trimetil-6-oksi-
1,2,3,4-tetragidrokhinolinom, Izv. AN SSSR.
Ser. khim., 1983, No. 10, pp. 2212-2218.
15. Tikhonov V.P., Zaveshchevskaya T.L.,
Sidlyarov D.P. Antioksidantnyi i
antigipoksantnyi kompleks na osnove
digidrokvertsetina dlya kosmeticheskikh izdelii,
pat. PCT/RU2009/000192 RF: WO
2009134165 A1. 05.11.2009.
16. Rozantsev E.G., Gagarina A.B.,
Kasaikina O.T. Ivanov Yu.A., Shapiro A.B.
Oksiproizvodnye-2,2,4-trimetil-1,2,3,4-tetragidrokhinolina,
kak antioksidanty dlya
karotinoidov i sposob ikh polucheniya , pat. SU
№ 548603. 28.023.77
17. Egorov I.A., Gulyushin S.Yu., Kovalev
V.O. Sposob stabilizatsii kombikormov , pat.
RF № 2329659. 27.07.2008.
18. Medvedeva S.M., Krysin M.Yu., Zubkov
F.I., Nikitina E.V., Shikhaliev Kh.S. Novye
geterotsiklicheskie sistemy na osnove
zameshchennykh 3,4-digidro-1Nspiro[
khinolin-2,1'-tsikloalkanov], Khimiya
geterotsiklicheskikh soedinenii, 2014, No. 9,
pp. 1388-1399.
19. Leshcheva E.V., Medvedeva S.M.,
Shikhaliev Kh.S. Sintez 4,4,6-trimetil-8-R-4Hpirrolo[
3,2,1-ij]khinolin-1,2-dionov , Zhurnal
organіchnoї ta farmatsevtichnoї khіmії, 2014,
No. 12, pp. 15-20.
20. Medvedeva S.M., Shikhaliev Kh.S.,
Leshcheva E.V., Solov'ev A.S. 4,4,6-Trimetil-
4H-pirrolo[3,2,1-ij]khinolin-1,2-diony v
reaktsiyakh tsiklokondensatsii s binukleofilami,
Vestn. Voronezh. gos. un-ta. Ser. Khimiya.
Biologiya. Farmatsiya, 2005, No. 2, pp. 54-59.
21. Medvedeva S.M., Shikhaliev Kh.S.,.
Sanina G.S, Solov'ev A.S. 4,4,6-Trimetil-1,2-
digidro-4H-pirrolo[3,2,1-ij]khinolin-1,2-diony
v trekhkomponentnykh reaktsiyakh
kondensatsii , Butlerovskie soobshcheniya,
2006, No 7, pp. 37-40.
22. Kojima E., Fujimori Sh., Awano K.
Cyclic anthranilic acid derivatives and process
for their preparation , pat. 5147874 US: Kyorin
Pharmaceutical Co., Ltd. 15.09.1992.
23. Kojima E., Saito K. Therapeutic agents of
metabolic bone disease , pat. EP 0402859 B1:
Kyorin Pharmaceutical Co., Ltd. 12.06.1990
24. Crumrine D.S., Dieschbourg T.A.,
O'Toole J.G., Tassone B.A., Vandeburg S.C.
Sodium Metal Promoted Condensations of
Carbamates, J. Org. Chem., 1987, No. 52, pp. 3699-3701.
25. Zhungietu G. I., Rekhter M. A. Izatin i
ego proizvodnye , Kishinev: Shtiintsa, 1977, 228 p.
26. Takhistov V.V. Prakticheskaya massspektrometriya
organicheskikh soedinenii , L.:
Izd-vo Leningr. un-ta, 1977, 268 p.
Published
2019-11-20
How to Cite
Medvedeva, S. M., Shikhaliev, K. S., Kryl’skii, D. V., & Siniaeva, L. A. (2019). Preparation and mass spectrometric analysis of 5,6- dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione and 1,1’- (1,2-dioxoethane-1,2-diyl)bis-1,2,3,4-tetrahydroquinoline. Sorbtsionnye I Khromatograficheskie Protsessy, 14(6). Retrieved from https://journals.vsu.ru/sorpchrom/article/view/1581
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