Home / Publications / The reaction of 1,5,6-trimethylbenzimidazole with 1,3-diphenylprop-2-yn-1-one and water: en route to β-amino enones and benzodiazocinones

The reaction of 1,5,6-trimethylbenzimidazole with 1,3-diphenylprop-2-yn-1-one and water: en route to β-amino enones and benzodiazocinones

Ludmila Viktorovna Andriyankova 1
Ludmila Viktorovna Andriyankova
Lina Pavlovna Nikitina 1
Lina Pavlovna Nikitina
Andrei Valer'evich Afonin 1
Andrei Valer'evich Afonin
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
Anastasiya Grigor'evna Mal'kina 1
Anastasiya Grigor'evna Mal'kina
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
Published 2015-07-08
CommunicationVolume 25, Issue 4, 254-256
5
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Belyaeva K. V. et al. The reaction of 1,5,6-trimethylbenzimidazole with 1,3-diphenylprop-2-yn-1-one and water: en route to β-amino enones and benzodiazocinones // Mendeleev Communications. 2015. Vol. 25. No. 4. pp. 254-256.
GOST all authors (up to 50) Copy
Belyaeva K. V., Andriyankova L. V., Nikitina L. P., Afonin A. V., Ushakov I. A., Mal'kina A. G., Trofimov B. A. The reaction of 1,5,6-trimethylbenzimidazole with 1,3-diphenylprop-2-yn-1-one and water: en route to β-amino enones and benzodiazocinones // Mendeleev Communications. 2015. Vol. 25. No. 4. pp. 254-256.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2015.07.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.006
TI - The reaction of 1,5,6-trimethylbenzimidazole with 1,3-diphenylprop-2-yn-1-one and water: en route to β-amino enones and benzodiazocinones
T2 - Mendeleev Communications
AU - Belyaeva, Kseniya Vasil'evna
AU - Andriyankova, Ludmila Viktorovna
AU - Nikitina, Lina Pavlovna
AU - Afonin, Andrei Valer'evich
AU - Ushakov, Igor Alekseevich
AU - Mal'kina, Anastasiya Grigor'evna
AU - Trofimov, Boris Aleksandrovich
PY - 2015
DA - 2015/07/08
PB - Mendeleev Communications
SP - 254-256
IS - 4
VL - 25
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2015_Belyaeva,
author = {Kseniya Vasil'evna Belyaeva and Ludmila Viktorovna Andriyankova and Lina Pavlovna Nikitina and Andrei Valer'evich Afonin and Igor Alekseevich Ushakov and Anastasiya Grigor'evna Mal'kina and Boris Aleksandrovich Trofimov},
title = {The reaction of 1,5,6-trimethylbenzimidazole with 1,3-diphenylprop-2-yn-1-one and water: en route to β-amino enones and benzodiazocinones},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.006},
number = {4},
pages = {254--256},
doi = {10.1016/j.mencom.2015.07.006}
}
MLA
Cite this
MLA Copy
Belyaeva, Kseniya Vasil'evna, et al. “The reaction of 1,5,6-trimethylbenzimidazole with 1,3-diphenylprop-2-yn-1-one and water: en route to β-amino enones and benzodiazocinones.” Mendeleev Communications, vol. 25, no. 4, Jul. 2015, pp. 254-256. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.006.

Abstract

Refluxing the mixture of 1,5,6-trimethylbenzimidazole, 1,3-diphenylprop-2-yn-1-one and water in MeCN for 70h affords (Z)-3-[2-(N-formyl-N-methylamino)-4,5-dimethylphenylamino]-1,3-diphenylprop-2-en-1-one (75%) and 1,8,9-trimethyl-3,5-diphenyl- 1,6-benzodiazocin-2(1H)-one (13%).

References

1.
(a) M. Adib, M. Mollahosseini, H. Yavari, M.H. Sayahi and H. R. Bijanzadeh, Synlett, 2004, 1086; (b) I. Yavari, M. Sabbaghan and Z. Hossaini, Synlett, 2006, 2501; (c) A. Shaabani, A.H. Rezayan, A. Sarvary, M. Heidary and S. W. Ng, Tetrahedron, 2009, 65, 6063; (d) Kh. Pourshamsian, N. Montazeri, S. Ali-Asgari, M.M. Zeydi and E. Biazar, Orient. J. Chem., 2011, 27, 1017; (e) Y. Shen, S. Cai, C. He, X. Lin, P. Lu and Y. Wang, Tetrahedron, 2011, 67, 8338; (f) K. V. Belyaeva, L.V. Andriyankova, L.P. Nikitina, A.G. Mal’kina, A.V. Afonin and B. A. Trofimov, Tetrahedron Lett., 2012, 53, 7040; (g) B. A. Trofimov, L.V. Andriyankova and K. V. Belyaeva, Chem. Heterocycl. Compd., 2012, 48, 147 (Khim. Geterotsikl. Soedin., 2012, 153) and references cited therein; (h) B. A. Trofimov, L.V. Andriyankova, L.P. Nikitina, K.V. Belyaeva, A.G. Mal’kina, A.V. Afonin and I. A. Ushakov, Synlett, 2012, 23, 2069; (i) K. V. Belyaeva, L.V. Andriyankova, L.P. Nikitina, G. Mal’kina, A.V. Afonin, I.A. Ushakov, I. Yu. Bagryanskaya and A. Trofimov, Tetrahedron, 2014, 70, 1091.
2.
Stereoselective Tandem Ring Opening of Imidazoles with Electron-Deficient Acetylenes and Water: Synthesis of Functionalized (Z,Z)-1,4-Diaza-2,5-dienes
Trofimov B.A., Andriyankova L.V., Nikitina L.P., Belyaeva K.V., Mal’kina A.G., Sobenina L.N., Afonin A.V., Ushakov I.A.
Organic Letters, 2013
4.
10.1016/j.mencom.2015.07.006_bib0020
Wallis
Acta Crystallogr., 1992
6.
(a) J. P. Vacca, J.S. Wai, L.S. Payne, R.C. A. Isaacs, W. Han, M. Egbertson and R. Pracitto, PCT Int. Appl., WO 2006121831 A2 20061116, 2006 (Chem. Abstr., 2006, 145, 505478); (b) S. Lohani, Z. Peng and A. E. Mckeown, U.S. Pat. Appl. Publ., US 20080280945 A1 20081113, 2008 (Chem. Abstr., 2008, 149, 556676); (c) R. C. A. Isaacs, J.S. Wai and T. E. Fisher, PCT Int. Appl., WO 2009154870 A1 20091223, 2009 (Chem. Abstr., 2009, 152, 97513).
7.
Stereoselective total synthesis of almorexant
Reddy N.S., Reddy B.V.
Tetrahedron Letters, 2014
8.
(a) S. I. Miller and R. Tanaka, in Selective Organic Transformations, ed. B. S. Thyagarajan, Wiley-Interscience, New York, 1970, vol. 1, p 143; J. I. Dickstein and S. I. Miller, in The Chemistry of the Carbon– Carbon Triple Bond, ed. S. Patai, Wiley, New York, 1978, vol. 2, p. 814.
9.
Stereoselective C(2)-Vinylation of 1-Substituted Imidazoles with 3-Phenyl-2-propynenitrile
Trofimov B.A., Andriyankova L.V., Belyaeva K.V., Mal’kina A.G., Nikitina L.P., Afonin A.V., Ushakov I.A.
Journal of Organic Chemistry, 2008
10.
Starikova O.V., Dolgushin G.V., Larina L.I., Komarova T.N., Lopyrev V.A.
Arkivoc, 2003
11.
10.1016/j.mencom.2015.07.006_bib0055
Zanina
Russ. Chem. Bull., 1995, 44, 689., 1995