Home / Publications / Acetylene based short route from 2,2,6,6-tetramethylpiperidin-4-one oxime to 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines

Acetylene based short route from 2,2,6,6-tetramethylpiperidin-4-one oxime to 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines

Denis Nikolaevich Tomilin 1
Denis Nikolaevich Tomilin
Olga Vital'evna Petrova 1
Olga Vital'evna Petrova
Arsalan Badmaevich Budaev 1
Arsalan Badmaevich Budaev
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
Guoqiang Q Yang 2
Guoqiang Q Yang
Rui Hu 2
Rui Hu
Published 2019-11-01
CommunicationVolume 29, Issue 6, 658-660
3
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Sagitova E. F. et al. Acetylene based short route from 2,2,6,6-tetramethylpiperidin-4-one oxime to 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines // Mendeleev Communications. 2019. Vol. 29. No. 6. pp. 658-660.
GOST all authors (up to 50) Copy
Sagitova E. F., Tomilin D. N., Petrova O. V., Budaev A. B., Sobenina L. N., Trofimov B. A., Yang G. Q., Hu R. Acetylene based short route from 2,2,6,6-tetramethylpiperidin-4-one oxime to 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines // Mendeleev Communications. 2019. Vol. 29. No. 6. pp. 658-660.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2019.11.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.11.018
TI - Acetylene based short route from 2,2,6,6-tetramethylpiperidin-4-one oxime to 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines
T2 - Mendeleev Communications
AU - Sagitova, Elena Faritovna
AU - Tomilin, Denis Nikolaevich
AU - Petrova, Olga Vital'evna
AU - Budaev, Arsalan Badmaevich
AU - Sobenina, Lyubov Nikolaevna
AU - Trofimov, Boris Aleksandrovich
AU - Yang, Guoqiang Q
AU - Hu, Rui
PY - 2019
DA - 2019/11/01
PB - Mendeleev Communications
SP - 658-660
IS - 6
VL - 29
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Sagitova,
author = {Elena Faritovna Sagitova and Denis Nikolaevich Tomilin and Olga Vital'evna Petrova and Arsalan Badmaevich Budaev and Lyubov Nikolaevna Sobenina and Boris Aleksandrovich Trofimov and Guoqiang Q Yang and Rui Hu},
title = {Acetylene based short route from 2,2,6,6-tetramethylpiperidin-4-one oxime to 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.11.018},
number = {6},
pages = {658--660},
doi = {10.1016/j.mencom.2019.11.018}
}
MLA
Cite this
MLA Copy
Sagitova, Elena Faritovna, et al. “Acetylene based short route from 2,2,6,6-tetramethylpiperidin-4-one oxime to 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines.” Mendeleev Communications, vol. 29, no. 6, Nov. 2019, pp. 658-660. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.11.018.

Abstract

Pharmaceutically relevant substituted 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo [3,2-c]pyridines have been assembled in good to excellent yields via the reaction of 2,2,6,6-tetramethylpiperidin-4-one oxime with acetylene, cross-coupling of the resulting 4,4,6,6-tetramethyl-4,5,6,7 tetrahydropyrrolo[3,2-c]pyridines with aroylbromoacetylenes, and reaction of the formed 2-(aroylethynyl)-4,4,6,6-tetramethyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines with hydrazine.

References

3.
Pyrrolizines: Design, synthesis, anticancer evaluation and investigation of the potential mechanism of action
Gouda A.M., Abdelazeem A.H., Omar H.A., Abdalla A.N., Abourehab M.A., Ali H.I.
Bioorganic and Medicinal Chemistry, 2017
4.
Pyrrolopyrimidines: An update on recent advancements in their medicinal attributes
6.
Recent advances of pyrrolopyridines derivatives: a patent and literature review
El-Gamal M.I., Anbar H.S.
Expert Opinion on Therapeutic Patents, 2017
8.
The Azaindole Framework in the Design of Kinase Inhibitors
Mérour J., Buron F., Plé K., Bonnet P., Routier S.
Molecules, 2014
9.
Pyrrolo[2,3-b]pyridine derivatives as potent Bruton’s tyrosine kinase inhibitors
Zhao X., Huang W., Wang Y., Xin M., Jin Q., Cai J., Tang F., Zhao Y., Xiang H.
Bioorganic and Medicinal Chemistry, 2015
10.
Exploring 6-Azaindole and 7-Azaindole Rings for Developing Cannabinoid Receptor 1 Allosteric Modulators
Immadi S.S., Dopart R., Wu Z., Fu B., Kendall D.A., Lu D.
Cannabis and Cannabinoid Research, 2018
11.
Exploring the third dimension
Kingwell K.
Nature Reviews Drug Discovery, 2009
12.
Discovery of selective and orally available spiro-3-piperidyl ATP-competitive MK2 inhibitors
Kaptein A., Oubrie A., Zwart E.D., Hoogenboom N., Wit J.D., Kar B.V., Hoek M.V., Vogel G., Kimpe V.D., Schultz-Fademrecht C., Borsboom J., Zeeland M.V., Versteegh J., Kazemier B., Roos J.D., et. al.
Bioorganic and Medicinal Chemistry Letters, 2011
13.
5-(2-Amino-pyrimidin-4-yl)-1H-pyrrole and 2-(2-amino-pyrimidin-4-yl)-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one derivatives as new classes of selective and orally available Polo-like kinase 1 inhibitors
Caruso M., Valsasina B., Ballinari D., Bertrand J., Brasca M.G., Caldarelli M., Cappella P., Fiorentini F., Gianellini L.M., Scolaro A., Beria I.
Bioorganic and Medicinal Chemistry Letters, 2012
14.
Cdc7 Kinase Inhibitors: Pyrrolopyridinones as Potential Antitumor Agents. 1. Synthesis and Structure–Activity Relationships
Vanotti E., Amici R., Bargiotti A., Berthelsen J., Bosotti R., Ciavolella A., Cirla A., Cristiani C., D’Alessio R., Forte B., Isacchi A., Martina K., Menichincheri M., Molinari A., Montagnoli A., et. al.
Journal of Medicinal Chemistry, 2008
15.
Constrained analogs of CB-1 antagonists: 1,5,6,7-Tetrahydro-4H-pyrrolo[3,2-c]pyridine-4-one derivatives
Smith R.A., Fathi Z., Brown S., Choi S., Fan J., Jenkins S., Kluender H.C., Konkar A., Lavoie R., Mays R., Natoli J., O’Connor S.J., Ortiz A.A., Podlogar B., Taing C., et. al.
Bioorganic and Medicinal Chemistry Letters, 2007
16.
Identification of 2-(4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-3-yl)-ethylamine derivatives as novel GnRH receptor antagonists
Chen M., Guo Z., Lanier M.C., Zhao L., Betz S.F., Huang C.Q., Loweth C.J., Ashweek N.J., Liu X., Struthers R.S., Bradbury M.J., Behan J.W., Wen J., O’Brien Z., Saunders J., et. al.
Bioorganic and Medicinal Chemistry Letters, 2007
17.
10.1016/j.mencom.2019.11.018_bib0045
Masood
Rasayan J. Chem., 2016
18.
J. L. Archibald and K. Heatherington, US Patent 3992544, 1976.
19.
Pyrrolo[3,2- c ]pyridine derivatives as inhibitors of platelet aggregation
Altomare C., Summo L., Cellamare S., Varlamov A.V., Voskressensky L.G., Borisova T.N., Carotti A.
Bioorganic and Medicinal Chemistry Letters, 2000
20.
Investigation on the antiplatelet activity of pyrrolo[3,2-c]pyridine-containing compounds
Voskressensky L.G., de Candia M., Carotti A., Borisova T.N., Kulikova L.N., Varlamov A.V., Altomare C.
Journal of Pharmacy and Pharmacology, 2003
21.
R. A. Smith, W.C. Wong, S.J. Olamovor, S. Choi, H.C. E. Kluender, Z. Zhang, R.C. Lavoie, J. Fan and B. L. Podlogar, WO Patent 03/027114A1, 2003.
22.
L. Cheng, US Patent 7576095B2, 2009.
23.
Pyrroles from ketoximes and acetylene. No. 36. 4,4,6,6-Tetramethyl-4,5,6,7-tetrahydro-5-azaindole, its nitroxyl and vinyl derivatives, and spin-labelled copolymer
Trofimov B.A., Shapiro A.B., Nesterenko R.N., Mikhaleva A.I., Kalabin G.A., Golovanova N.I., Yakovleva I.V., Korostova S.E.
Chemistry of Heterocyclic Compounds, 1988
24.
Stereochemical aspects of pyrrole formation from substituted piperidin-4-one oximes and acetylene
Trofimov B.A., Vasil'tsov A.M., Mikhaleva A.I., Kalabin G.A., Shcherbakov V.V., Nesterenko R.N., Polubentsev E.A., Praliev K.D.
Chemistry of Heterocyclic Compounds, 1991
25.
10.1016/j.mencom.2019.11.018_sbref0070c
Varlamov
Synthesis, 2002
26.
TANDEM MICHAEL ADDITION - HOFFMAN ELIMINATION SEQUENCE OF DMAD ON TETRAHYDROPYRROLO[3,2-C]PYRIDINES. NEW ROUTE TO VINYLPYRROLES .
Varlamov A.V., Borisova T.N., Voskressensky L.G., Nsabimana B., Chernyshev A.I.
Heterocyclic Communications, 2001
27.
Borisova T.N., Voskressensky L.G., Soklakova T.A., Nsabimana B., Varlamov A.V.
Mendeleev Communications, 2002
28.
The first synthesis and X-ray crystal structure of tetrahydropyrrolo[2,3-d]azocines
Varlamov A.V., Borisova T.N., Voskressensky L.G., Soklakova T.A., Kulikova L.N., Chernyshev A.I., Alexandrov G.G.
Tetrahedron Letters, 2002
30.
Tandem transformations of tetrahydropyrrolo[3,2-c]pyridines under the action of dimethyl acetylenedicarboxylate. A novel route to pyrrolo[2,3-d]azocines
Voskressensky L.G., Borisova T.N., Vorob’eva T.A., Chernyshev A.I., Varlamov A.V.
Russian Chemical Bulletin, 2005
31.
First Efficient One-Pot Synthesis of Tetrahydropyrrolo[2,3-d]azocines and Tetrahydroazocino[4,5-b]indoles
Voskressensky L., Borisova T., Soklakova T., Kulikova L., Borisov R., Varlamov A.
Letters in Organic Chemistry, 2005
32.
Transformations of 2-trifluoroacetyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridines by the action of ethyl propynoate. A novel synthesis of 2-trifluoroacetyl-4,7,8,9-tetrahydro-1H-pyrrolo[2,3-d]azocines
Voskresenskii L.G., Borisova T.N., Vorob’eva T.A., Grishachkina O.V., Kulikova L.N., Chernyshev A.I., Varlamov A.V.
Russian Journal of Organic Chemistry, 2006
33.
10.1016/j.mencom.2019.11.018_sbref0075h
Voskressensky
2008
34.
Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal ‘inverse Sonogashira coupling’
Trofimov B.A., Stepanova Z.V., Sobenina L.N., Mikhaleva A.I., Ushakov I.A.
Tetrahedron Letters, 2004
35.
Trofimov B.A., Stepanova Z.V., Sobenina L.N., Mikhaleva A.I., Sinegovskaya L.M., Potekhin K.A., Fedyanin I.V.
Mendeleev Communications, 2005
36.
10.1016/j.mencom.2019.11.018_sbref0080c
Trofimov
2009
37.
Tomilin D.N., Soshnikov D.Y., Trofimov A.B., Gotsko M.D., Sobenina L.N., Ushakov I.A., Afonin A.V., Koldobsky A.B., Vitkovskaya N.M., Trofimov B.A.
Mendeleev Communications, 2016
38.
A highly selective fluorescent sensor for fluoride anion based on pyrazole derivative: Naked eye “no–yes” detection
Yang Z., Zhang K., Gong F., Li S., Chen J., Ma J.S., Sobenina L.N., Mikhaleva A.I., Trofimov B.A., Yang G.
Journal of Photochemistry and Photobiology A: Chemistry, 2011