Home / Publications / Selective one-pot synthesis of 11-arylmethylidene-11H-isoindolo-[2,1-a]benzimidazoles and 6-arylbenzimidazo[2,1-a]isoquinolines from o-alkynylbenzaldehydes and o-diaminobenzenes

Selective one-pot synthesis of 11-arylmethylidene-11H-isoindolo-[2,1-a]benzimidazoles and 6-arylbenzimidazo[2,1-a]isoquinolines from o-alkynylbenzaldehydes and o-diaminobenzenes

Valentin Dmitrievich Gvozdev 1
Valentin Dmitrievich Gvozdev
, 
Konstantin Nikolaevich Shavrin 1
Konstantin Nikolaevich Shavrin
, 
Esfir Grigor'evna Baskir 1
Esfir Grigor'evna Baskir
, 
Mikhail Petrovich Egorov 1
Mikhail Petrovich Egorov
, 
Oleg Matveevich Nefedov 1
Oleg Matveevich Nefedov
10.1016/j.mencom.2017.05.004
Published 2017-04-25
Communication , Volume 27, Issue 3, 231-233
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Gvozdev V. D. et al. Selective one-pot synthesis of 11-arylmethylidene-11H-isoindolo-[2,1-a]benzimidazoles and 6-arylbenzimidazo[2,1-a]isoquinolines from o-alkynylbenzaldehydes and o-diaminobenzenes // Mendeleev Communications. 2017. Vol. 27. No. 3. pp. 231-233.
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Gvozdev V. D., Shavrin K. N., Baskir E. G., Egorov M. P., Nefedov O. M. Selective one-pot synthesis of 11-arylmethylidene-11H-isoindolo-[2,1-a]benzimidazoles and 6-arylbenzimidazo[2,1-a]isoquinolines from o-alkynylbenzaldehydes and o-diaminobenzenes // Mendeleev Communications. 2017. Vol. 27. No. 3. pp. 231-233.
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TY - JOUR
DO - 10.1016/j.mencom.2017.05.004
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.004
TI - Selective one-pot synthesis of 11-arylmethylidene-11H-isoindolo-[2,1-a]benzimidazoles and 6-arylbenzimidazo[2,1-a]isoquinolines from o-alkynylbenzaldehydes and o-diaminobenzenes
T2 - Mendeleev Communications
AU - Gvozdev, Valentin Dmitrievich
AU - Shavrin, Konstantin Nikolaevich
AU - Baskir, Esfir Grigor'evna
AU - Egorov, Mikhail Petrovich
AU - Nefedov, Oleg Matveevich
PY - 2017
DA - 2017/04/25
PB - Mendeleev Communications
SP - 231-233
IS - 3
VL - 27
ER -
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@article{2017_Gvozdev,
author = {Valentin Dmitrievich Gvozdev and Konstantin Nikolaevich Shavrin and Esfir Grigor'evna Baskir and Mikhail Petrovich Egorov and Oleg Matveevich Nefedov},
title = {Selective one-pot synthesis of 11-arylmethylidene-11H-isoindolo-[2,1-a]benzimidazoles and 6-arylbenzimidazo[2,1-a]isoquinolines from o-alkynylbenzaldehydes and o-diaminobenzenes},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.004},
number = {3},
pages = {231--233},
doi = {10.1016/j.mencom.2017.05.004}
}
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Gvozdev, Valentin Dmitrievich, et al. “Selective one-pot synthesis of 11-arylmethylidene-11H-isoindolo-[2,1-a]benzimidazoles and 6-arylbenzimidazo[2,1-a]isoquinolines from o-alkynylbenzaldehydes and o-diaminobenzenes.” Mendeleev Communications, vol. 27, no. 3, Apr. 2017, pp. 231-233. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.004.

Abstract

Cyclization of o-alkynylbenzaldehydes with o-diaminobenzenes in DMSO under the sequential action of NH4Br and K2CO3 affords 11-arylmethylidene-11H-isoindolo[2,1-a]-benzimidazoles as a result of 5-exo-dig ring closure; whereas replacement of treating with K2CO3 by heating at 110–115°C results in 6-endo-dig cyclization with formation of 6-arylbenzimidazo[2,1-a]isoquinolines.

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