Home / Publications / Stereoselective one-pot synthesis of (1Z)- and (1E)-1-arylmethylidene-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles by cyclization of alk-4-ynals with o-diaminobenzene

Stereoselective one-pot synthesis of (1Z)- and (1E)-1-arylmethylidene-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles by cyclization of alk-4-ynals with o-diaminobenzene

Valentin Dmitrievich Gvozdev 1
Valentin Dmitrievich Gvozdev
, 
Konstantin Nikolaevich Shavrin 1
Konstantin Nikolaevich Shavrin
, 
Mikhail Petrovich Egorov 1
Mikhail Petrovich Egorov
, 
Oleg Matveevich Nefedov 1
Oleg Matveevich Nefedov
10.1016/j.mencom.2016.01.002
Published 2015-12-30
Communication , Volume 26, Issue 1, 3-5
8
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Gvozdev V. D. et al. Stereoselective one-pot synthesis of (1Z)- and (1E)-1-arylmethylidene-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles by cyclization of alk-4-ynals with o-diaminobenzene // Mendeleev Communications. 2015. Vol. 26. No. 1. pp. 3-5.
GOST all authors (up to 50) Copy
Gvozdev V. D., Shavrin K. N., Egorov M. P., Nefedov O. M. Stereoselective one-pot synthesis of (1Z)- and (1E)-1-arylmethylidene-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles by cyclization of alk-4-ynals with o-diaminobenzene // Mendeleev Communications. 2015. Vol. 26. No. 1. pp. 3-5.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2016.01.002
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.01.002
TI - Stereoselective one-pot synthesis of (1Z)- and (1E)-1-arylmethylidene-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles by cyclization of alk-4-ynals with o-diaminobenzene
T2 - Mendeleev Communications
AU - Gvozdev, Valentin Dmitrievich
AU - Shavrin, Konstantin Nikolaevich
AU - Egorov, Mikhail Petrovich
AU - Nefedov, Oleg Matveevich
PY - 2015
DA - 2015/12/30
PB - Mendeleev Communications
SP - 3-5
IS - 1
VL - 26
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2015_Gvozdev,
author = {Valentin Dmitrievich Gvozdev and Konstantin Nikolaevich Shavrin and Mikhail Petrovich Egorov and Oleg Matveevich Nefedov},
title = {Stereoselective one-pot synthesis of (1Z)- and (1E)-1-arylmethylidene-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles by cyclization of alk-4-ynals with o-diaminobenzene},
journal = {Mendeleev Communications},
year = {2015},
volume = {26},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.01.002},
number = {1},
pages = {3--5},
doi = {10.1016/j.mencom.2016.01.002}
}
MLA
Cite this
MLA Copy
Gvozdev, Valentin Dmitrievich, et al. “Stereoselective one-pot synthesis of (1Z)- and (1E)-1-arylmethylidene-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles by cyclization of alk-4-ynals with o-diaminobenzene.” Mendeleev Communications, vol. 26, no. 1, Dec. 2015, pp. 3-5. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.01.002.

Abstract

Cyclization of alk-4-ynals with o-diaminobenzene in DMSO under the sequential action of NH4Br and base (KOH or K2CO3) affords 1-arylmethylidene-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles, which are formed selectively as E- or Z-isomers depending on the base used.

References

2.
Discovery of novel inhibitors of the ZipA/FtsZ complex by NMR fragment screening coupled with structure-based design
Tsao D.H., Sutherland A.G., Jennings L.D., Li Y., Rush T.S., Alvarez J.C., Ding W., Dushin E.G., Dushin R.G., Haney S.A., Kenny C.H., Karl Malakian A., Nilakantan R., Mosyak L.
Bioorganic and Medicinal Chemistry, 2006
3.
H. Uchida, A. Asagarasu and T. Matsui, US Patent Application 2013/0079306 A1.
4.
E. B. Skibo, US Patent 6,998,413, 2006 (Chem. Abstr., 2006, 133, 12985).
6.
Rhodium catalyzed enantioselective cyclization of substituted imidazoles via C–H bond activation
Tsai A.S., Wilson R.M., Harada H., Bergman R.G., Ellman J.A.
Chemical Communications, 2009
7.
Synthesis of annulated benzimidazoles via amidine cyclization
Liubchak K., Nazarenko K., Tolmachev A.
Tetrahedron, 2012
9.
Synthesis of condensed heterocycles via cyclopropylimine rearrangement of cyclopropylazoles
Tomilov Y.V., Platonov D.N., Frumkin A.E., Lipilin D.L., Salikov R.F.
Tetrahedron Letters, 2010
10.
Aromatic homolytic substitution using solid phase synthesis
Allin S.M., Bowman W.R., Karim R., Rahman S.S.
Tetrahedron, 2006
11.
An Effective Synthetic Entry to Fused Benzimidazoles via Iodocyclization
Zhang X., Zhou Y., Wang H., Guo D., Ye D., Xu Y., Jiang H., Liu H.
Advanced Synthesis and Catalysis, 2011
16.
Efficient and Inexpensive Synthesis of Benzimidazoles and Quinoxalines
Raju B.C., Theja N.D., Kumar J.A.
Synthetic Communications, 2008
18.
Base-Mediated Chemo- and Stereoselective Addition of 5-Aminoindole/Tryptamine and Histamines onto Alkynes
Verma A.K., Patel M., Joshi M., Likhar P.R., Tiwari R.K., Parang K.
Journal of Organic Chemistry, 2013