Home / Publications / Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations

Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations

Orudzh Garib ogly Nabiev 1
Orudzh Garib ogly Nabiev
, 
Zargalam O Nabizade 1
Zargalam O Nabizade
, 
Remir Grigorevich Kostyanovsky 1
Remir Grigorevich Kostyanovsky
10.1016/j.mencom.2009.09.018
Published 2009-09-15
Communication , Volume 19, Issue 5, 281-283
11
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Nabiev O. G. O., Nabizade Z. O., Kostyanovsky R. G. Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations // Mendeleev Communications. 2009. Vol. 19. No. 5. pp. 281-283.
GOST all authors (up to 50) Copy
Nabiev O. G. O., Nabizade Z. O., Kostyanovsky R. G. Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations // Mendeleev Communications. 2009. Vol. 19. No. 5. pp. 281-283.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2009.09.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.09.018
TI - Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations
T2 - Mendeleev Communications
AU - Nabiev, Orudzh Garib ogly
AU - Nabizade, Zargalam O
AU - Kostyanovsky, Remir Grigorevich
PY - 2009
DA - 2009/09/15
PB - Mendeleev Communications
SP - 281-283
IS - 5
VL - 19
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2009_Nabiev,
author = {Orudzh Garib ogly Nabiev and Zargalam O Nabizade and Remir Grigorevich Kostyanovsky},
title = {Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations},
journal = {Mendeleev Communications},
year = {2009},
volume = {19},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.09.018},
number = {5},
pages = {281--283},
doi = {10.1016/j.mencom.2009.09.018}
}
MLA
Cite this
MLA Copy
Nabiev, Orudzh Garib ogly, et al. “Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations.” Mendeleev Communications, vol. 19, no. 5, Sep. 2009, pp. 281-283. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.09.018.

Abstract

Simple and efficient methods have been developed to obtain cyanomethylamines and azidomethylamines using reactions of methoxymethylamines with TMSCN and TMSN3, respectively. In the case of dimethylformamide dimethylacetal, only one MeO group was substituted with CN, and an unexpected direction of the subsequent azidation was found. Adducts of azidomethylamines with DMAD were studied, and the base-catalyzed isomerization of symmetric triazoles into non-symmetric ones was revealed.

References

1.
Shtamburg V.G., Shishkin O.V., Zubatyuk R.I., Kravchenko S.V., Tsygankov A.V., Shtamburg V.V., Distanov V.B., Kostyanovsky R.G.
Mendeleev Communications, 2007
2.
Ring-Fused Cyclopropanone N,O-Acetals. Electrochemical Preparation and Their Reactivities under Acidic Conditions
Chiba T., Saitoh I., Okimoto M., Tanase T., Yano S.
Journal of Organic Chemistry, 1999
3.
Some recent applications of α-amino nitrile chemistry
Enders D., Shilvock J.P.
Chemical Society Reviews, 2000
6.
The synthesis of alkyl aryl nitriles from N-(1-arylalkylidene)cyanomethylamines. Part 2. Mechanism
Perosa A., Selva M., Tundo P.
Journal of the Chemical Society Perkin Transactions 2, 2002
7.
Systemes de strecker et apparentes - VII
Bejaud M., Mion L., Commeyras A.
Tetrahedron Letters, 1975
14.
A simple one-pot procedure for the direct conversion of alcohols into azides using TsIm
Soltani Rad M.N., Behrouz S., Khalafi-Nezhad A.
Tetrahedron Letters, 2007
15.
Effect of carbonates/phosphates as nucleophilic catalysts in dimethylformamide for efficient cyanosilylation of aldehydes and ketones
Prakash G.K., Vaghoo H., Panja C., Surampudi V., Kultyshev R., Mathew T., Olah G.A.
Proceedings of the National Academy of Sciences of the United States of America, 2007
16.
10.1016/j.mencom.2009.09.018_bib5_1
Nabiev
Dokl. Akad. Nauk SSSR, 1985
17.
Macroheterocycles; XIV. A Convenient Synthesis of Azacrown Ether Derivatives via Aminomethylation
Bogatsky A.V., Lukyanenko N.G., Pastushok V.N., Kostyanovsky R.G.
Synthesis, 1983
18.
10.1016/j.mencom.2009.09.018_bib5_3
Bogatsky
Dokl. Akad. Nauk SSSR, 1982
19.
10.1016/j.mencom.2009.09.018_bib5_4
Kostyanovskii
Izv. Akad. Nauk SSSR, Ser. Khim., 1974
20.
10.1016/j.mencom.2009.09.018_bib5_5
Kostyanovskii
Izv. Akad. Nauk SSSR, Ser. Khim., 1965
21.
10.1016/j.mencom.2009.09.018_bib5_6
Kostyanovskii
Izv. Akad. Nauk SSSR, Otdel. Khim. Nauk., 1963