Nitro and aminobenzimidazoles

Viktor Milata

doi:10.2478/acs-2018-0026

.blurhash-client-img { display: none !important; }

Nitro and aminobenzimidazoles

Acta Chimica Slovaca

Volume 11 (2018): Issue 2 (October 2018)

By: Viktor Milata

Open Access

|Dec 2018

Abstract

A summary of the preparation methods of 2 tautomeric and 4 N-methylated benzimidazoles with a nitro group on the benzene ring (1–6) and with an amino group in the same positions (7–12) were summarized. Annular tautomerism of the title compounds 1–12 has been studied using ¹H, ¹³C and ¹⁵N NMR spectra in liquid and solid state (CPMAS), UV spectra and quantum chemical calculations.

References

Bella M, Milata V (2008) J. Heterocycl. Chem. 45: 425–427.10.1002/jhet.5570450220
Search in Google Scholar Back to article
Claramunt RM, Cornago P, Santa María MD, Torres V, Pinilla E, Torres MR, Elguero J (2006) Supramol. Chem. 18: 349–356.10.1080/10610270600594865
Search in Google Scholar Back to article
Cornago P, Cabildo P, Claramunt RM, Bouissane L, Pinilla E, Torres MR, Elguero J (2009) New J. Chem. 33: 125–135. 10.1039/b812018h, CSD version 5.29, January 2008 update.10.1039/B812018H
Search in Google Scholar Back to article
Allen FH, Acta Crystallogr. Sect. B 2002; B58: 380–388.10.1107/S0108768102003890
Search in Google Scholar Back to article
Allen FH, Motherwell WDS, Acta Crystallogr. Sect. B 2002; B58: 407–422.10.1107/S0108768102004895
Search in Google Scholar Back to article
Denmlow EV, Richter R, Zhivich AB (1993) J. Chem. Res. (S) 504–505.
Search in Google Scholar Back to article
Efros LS (1953) J. Gen. Chem. 23: 957–963 (translated p. 995).
Search in Google Scholar Back to article
Efros LS, Ionin BI (1957) J. Gen. Chem. 27: 406–411 (translated p. 459).
Search in Google Scholar Back to article
Elguero J, Marzin C, Katritzky AR, Linda P (1976) The Tautomerism of Heterocycles, Adv. Heterocyclic Chem., Academic Press, New York, Suppl. 1: 266–300.
Search in Google Scholar Back to article
Ellis GP, Jones RT (1974) J. Chem. Soc. Perkin Trans. I, 903–909.10.1039/p19740000903
Search in Google Scholar Back to article
Fruchier A, Pappalardo L, Elguero J (1980) Ann. Quim. 76: 79–84.
Search in Google Scholar Back to article
Garcia MÁ, Claramunt RM, Solčan T, Milata V, Alkotra I, Elguero J (2009) Magn. Reson. Chem. 47: 100–104. Haque MR, Rasmussen M (1993) Aust. J. Chem. 47: 1523–1526.10.1002/mrc.2357
Search in Google Scholar Back to article
Houben L, Ramaekers R, Adamowicz, Maes G (2004) Internet Electron. J. Mol. Des. 3: 163–181, http://www.biochempress.com.
Search in Google Scholar Back to article
Howell JR, Rasmussen M (1993) Aust. J. Chem. 46: 1177–1191.10.1071/CH9931177
Search in Google Scholar Back to article
Joseph L, Julca J (1962) J. Org. Chem. 27: 1101–1102.10.1021/jo01050a549
Search in Google Scholar Back to article
Kada R, Jurášek A, Kováč J, Králik P (1974) Chem. Zvesti 28: 391–395.
Search in Google Scholar Back to article
Leandri G, Mangini A, Montanari F, Passerini R (1955) Gazz. Chim. Ital. 85: 769–814.
Search in Google Scholar Back to article
Li JJ (2009) Gould–Jacobs reaction. In: Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications (4th ed.). Springer-Verlag. p 263 doi: 10.1007/978-3-642-01053-8_113. ISBN 9783642010538.10.1007/978-3-642-01053-8_113
Search in Google Scholar Back to article
López-Alvarado P, Avendaño C, Menéndez JC (1991) Heterocycles 32: 1003–1012.10.3987/COM-91-5720
Search in Google Scholar Back to article
Lythgoe DJ, McClenaghan I, Ramsden CA (1993) J. Heterocycl. Chem. 30: 113–117.10.1002/jhet.5570300120
Search in Google Scholar Back to article
Marcos A, Pedregal C, Avendaño C (1991) Tetrahedron 47: 7459–7464.10.1016/S0040-4020(01)89747-7
Search in Google Scholar Back to article
Milata V, Ilavský D (1993) Org. Prep. Proc. Int. 25: 703–704.10.1080/00304949309356271
Search in Google Scholar Back to article
Milata V, Ilavský D (1996) Bull. Soc. Chim. Belg., 105: 213–214.
Search in Google Scholar Back to article
Milata V, Ilavský D, Goljer I (1989) Coll. Czech. Chem. Commun. 54: 713–724.10.1135/cccc19890713
Search in Google Scholar Back to article
Pappalardo L, Elguero J, Fruchier A (1975) An. Quim. 71: 598–602.
Search in Google Scholar Back to article
Rabinowitz JL, Wagner EC (1951) J. Amer. Chem. Soc. 73: 3030–3035.10.1021/ja01151a017
Search in Google Scholar Back to article
Ramaekers R, Houben L, Adamowicz, Maes G (2003) Vibrat. Spectrosc. 32: 185–197.10.1016/S0924-2031(03)00061-4
Search in Google Scholar Back to article
Reddy VM, Reddy K (1979) Indian J. Chem. 17B: 357–359.
Search in Google Scholar Back to article
Van der Want (1947) Rec.Trav. Chim. 67: 45–51.10.1002/recl.19480670107
Search in Google Scholar Back to article
Zincke T, Helmert B (1896) J. Prakt. Chem. 2, 53: 91–106.10.1002/prac.18960530108
Search in Google Scholar Back to article

Articles in this issue

DOI: https://doi.org/10.2478/acs-2018-0026 | Journal eISSN: 1339-3065 | Journal ISSN: 1337-978X

Journal RSS Feed

Language: English

Page range: 182 - 188

Published on: Dec 19, 2018

Published by: Slovak University of Technology in Bratislava

In partnership with: Paradigm Publishing Services

Publication frequency: 1 issue per year

Keywords:

X-Nitro-1-methylbenzimidazoles,

X-amino-1-methylbenzimidazoles,

NMR,

Related subjects:

© 2018 Viktor Milata, published by Slovak University of Technology in Bratislava
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Volume 11 (2018): Issue 2 (October 2018)