Keywords
alkylation
heterocyclization
hydrazines
pyrano[3,4-c]pyridines
pyrano[3,4-c]thieno[3,2-e][1,2,4]triazolo[4,3-a]pyridines
thiones
triazolo[4,3-a]pyridines
Abstract
New effective synthesis of functionalized pyrano[3,4-c]thieno-[3,2-e][1,2,4]triazolo[4,3-a]pyridines comprises nucleophilic substitution in 8-morpholino-6-thioxopyrano[3,4-c]pyridine-5-carbonitrile with hydrazine hydrate followed by sequential heterocyclization with formic acid and chloroacetic acid derivatives.
References
1.
10.1016/j.mencom.2020.03.017_bib0005
Eicher
The Chemistry of Heterocycles. Structure, Reactions, Synthesis, and Applications,
2003
2.
Azarifar D., Ghaemi M., Golbaghi M., Karamian R., Asadbegy M.
RSC Advances,
2016
3.
Nguyen S.T., Kwasny S.M., Ding X., Cardinale S.C., McCarthy C.T., Kim H., Nikaido H., Peet N.P., Williams J.D., Bowlin T.L., Opperman T.J.
Bioorganic and Medicinal Chemistry,
2015
4.
Zhao J., Fang L., Zhang X., Liang Y., Gou S.
Bioorganic and Medicinal Chemistry,
2016
5.
Prakash O., Hussain K., Aneja D.K., Sharma C., Aneja K.R.
Organic and Medicinal Chemistry Letters,
2011
6.
Arabshahi H.J., Leung E., Barker D., Reynisson J.
MedChemComm,
2014
7.
Abdelaziz M.E., El-Miligy M.M., Fahmy S.M., Mahran M.A., Hazzaa A.A.
Bioorganic Chemistry,
2018
8.
Reddy B.V., Reddy S.G., Reddy M.R., Sridhar B., Bhadra M.P.
Tetrahedron Letters,
2014
9.
Paronikyan E.G., Dashyan S.S., Noravyan A.S., Tamazyan R.A., Ayvazyan A.G., Panosyan H.A.
Tetrahedron,
2015
10.
Panda B., Sarkar T.K.
Tetrahedron Letters,
2008
11.
Suzdalev K.F., Krachkovskaya A.V., Borodkin G.S., Galenko-Yaroshevsky P.A., Tikhonov A.V., Kurbatov S.V.
Mendeleev Communications,
2019
12.
Schmidt M.A., Qian X.
Tetrahedron Letters,
2013
13.
Reichelt A., Falsey J.R., Rzasa R.M., Thiel O.R., Achmatowicz M.M., Larsen R.D., Zhang D.
Organic Letters,
2010
14.
Kirsch G., Abdelwahab A., Hanna A.
Synthesis,
2017
15.
Grigor’ev A.A., Karpov S.V., Kayukov Y.S., Nasakin O.E., Gracheva I.A., Tafeenko V.A.
Chemistry of Heterocyclic Compounds,
2017
16.
Kalugin V.E., Shestopalov A.M.
Russian Chemical Bulletin,
2019
17.
Paronikyan E.G., Dashyan S.S., Minasyan N.S., Stepanyan G.M., Ayvazyan A.G., Tamazyan R.A.
Chemistry of Heterocyclic Compounds,
2016
18.
Paronikyan E.G., Mirzoyan G.V., Noravyan A.S., Arzanunts É.M., Sukasyan R.S., Sarkisyan I.S., Nazaryan I.M., Dzhagatspanyan I.A.
Pharmaceutical Chemistry Journal,
1997
19.
Paronikyan E.G., Noravyan A.S.
Chemistry of Heterocyclic Compounds,
1999
20.
Paronikyan E.G., Sirakanyan S.N., Noravyan A.S., Paronikyan R.G., Dzhagatspanyan I.A.
Pharmaceutical Chemistry Journal,
2001