European Journal of Chemistry 2015, 6(2), 219-224 | doi: https://doi.org/10.5155/eurjchem.6.2.219-224.1223 | Get rights and content

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Utility of 2-cyano-N-(2-hydroxyethyl) acetamide in heterocyclic synthesis


Moustafa Ahmed Gouda (1,*) , Meshal Abdulrahim Sabah (2) , Waled Khaled Aljuhani (3) , Ahmed Saleh El-Gahani (4) , Snad Abd El-Karem El-Enazi (5) , Salem Atalleh Al Enizi (6) , Majed Musallam Al-Balawi (7)

(1) Chemistry Department, Faculty of Science, Mansoura University, Mansoura, 35516, Egypt
(2) Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
(3) Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
(4) Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
(5) Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
(6) Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
(7) Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
(*) Corresponding Author

Received: 19 Nov 2014 | Revised: 28 Dec 2014 | Accepted: 03 Jan 2015 | Published: 30 Jun 2015 | Issue Date: June 2015

Abstract


This review presents a systematic and comprehensive survey of the method of preparation and the chemical reactivity of 2-cyano-N-(2-hydroxyethyl) acetamide. The target compounds are important intermediates for the synthesis of a variety of synthetically useful and novel heterocyclic systems.


Keywords


Reactivity; Synthesis; Ethanolamine; Cyanoacetylation; Fused heterocycles; 2-Cyano-N-(2-hydroxyethyl) acetamide

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DOI: 10.5155/eurjchem.6.2.219-224.1223

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[4]. Moustafa Ahmed Gouda, Meshal Abdulrahim Sabah, Waled Khaled Aljuhani, Ahmed Saleh El-Gahani, Snad Abd El-Karem El-Enazi, Salem Atalleh Al Enizi, Majed Musallam Al-Balawi
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References


[1]. Elgemeie, G. H.; Elghandour, A. H.; Elzanate, A. M.; Ahmed, S. A. J. Chem. Soc. Perkin Trans I 1997, 21, 3285-3290

[2]. Milad, R. M.; Zaki, H. S.; Ibrahim, S. A. J. Chem. Res. (S) 1992, 5, 154-155.

[3]. Kim, C. K.; Zielinski, P. A.; Maggiulli, A. C. J. Org. Chem. 1984, 49, 5247-5250.
http://dx.doi.org/10.1021/jo00200a047

[4]. Elgemeie, G. H.; Elzanaty, A. M.; Elghandour, A. H.; Ahmed, S. A. Synth. Commun. 2006, 36, 825-834.
http://dx.doi.org/10.1080/00397910500449534

[5]. Dankova, E. F.; Bakulev, V. A.; Grishakov, A. N.; Mokrushin, V. S. Izv. Akad. Nauk. SSSR. Ser. Khim. 1988, 5, 1126-1128

[6]. Hawes, E. M.; Gorecki, D. K. J.; Gedir, G. G. J. Med. Chem, 1977, 20, 838-841.
http://dx.doi.org/10.1021/jm00216a021

[7]. Mijin, D.; Marinkovic, A. Synth. Commun. 2006, 36, 193-198.
http://dx.doi.org/10.1080/00397910500334421

[8]. Zhuravel, I.; Kovalenko, M. S.; Ivachtchenko, V. A.; Balakin, K. V.; Kazmirchuk, V. V. Bioorg. Med. Chem. 2005, 15, 5483-5487.
http://dx.doi.org/10.1016/j.bmcl.2005.08.081

[9]. Geissler, A. E.; Huppatz, J. L.; Phillips, J. N. Pesticide Sci. 1980, 11, 432-438.
http://dx.doi.org/10.1002/ps.2780110410

[10]. Roifman, C. M.; Aviv, G.; Alexander, L. PCT. Int. Appl. WO Patent, 2000, 0055, 128; Chem. Abstr. 2000, 133, 237695h.

[11]. Fahmy, H. T. Y.; Rostom, S. A. F.; Bekhit, A. A. Archiv der Pharm. 2002, 335, 213-322.
http://dx.doi.org/10.1002/1521-4184(200205)335:5<213::AID-ARDP213>3.0.CO;2-H

[12]. Ismail, M. M. F.; Ammar, Y. A.; El-Zahaby, H. S. A.; Eisa, S. I.; Barakat, S. E. Arch. Pharm. Life Sci. 2007, 340, 476-482.
http://dx.doi.org/10.1002/ardp.200600197

[13]. Doemling, A.; Wang, K.; Herdtweck, E. ACS Comb. Sci. 2012, 14, 316-322.
http://dx.doi.org/10.1021/co3000133

[14]. Horecker, B. L.; Kornberg, A. J. Biol. Chem. 1948, 175, 385-390.

[15]. Pearson, J. C.; Weaver, M. A.; Fleischer, J. C.; King, G. A. US 2006/115516.

[16]. Gillen, K. J.; Jamieson, C.; Maclean, J. K. F.; Moir, E. M.; Rankovic, Z. Patent; N. V. Organon, 2008, WO2008/3452.

[17]. Osdene, T. S.; Santilli, A. A.; McCardle, L. E.; Rosenthale, M. E. J. Med. Chem. 1967, 10, 165-171.
http://dx.doi.org/10.1021/jm00314a008

[18]. Tilak, B. D.; Ayyangar, N. R.; Rao, U. S. Indian J. Chem. B 1984, 23, 18-23.

[19]. Manidhar, D. M.; Rao, K. U. M.; Reddy, N. B.; Sundar, C. S.; Reddy, C. S. J. Korean. Chem. Soc. 2012, 56, 459-463.

[20]. Ivanov, E. I.; Kalayanov, G. D.; Yaroshchenko, I. M. Zh. Org. Khim. 1989, 25, 1975-1975.

[21]. Rideau, E.; Smith, T. K.; Stewart, G.; Westwood, N. J.; Zhou, L.; Rideau, E.; Smith, T. K. A. J. Med. Chem. 2013, 56, 796-806.
http://dx.doi.org/10.1021/jm301215e

[22]. Doemling, A.; Wang, K.; Herdtweck, E. ACS Comb. Sci. 2011, 13, 140-146.
http://dx.doi.org/10.1021/co100040z

[23]. Doemling, A.; Kim, D.; Wang, K. J. Comb. Chem. 2010, 12, 111-118
http://dx.doi.org/10.1021/cc9001586

[24]. Dannhardt, G.; Dominiak, P.; Laufer, S. Arch. Pharm. 1991, 324, 141-148.
http://dx.doi.org/10.1002/ardp.19913240303

[25]. Endo, S.; Hu, D.; Suyama, M.; Matsunaga, T.; Sugimoto, K.; Matsuya, Y.; El-Kabbani, O.; Kuwata, K.; Hara, A.; Kitade, Y.; Toyooka, N. Bioorg. Med. Chem. 2013, 21, 6378-6384.
http://dx.doi.org/10.1016/j.bmc.2013.08.059

[26]. Areias, F.; Costa, M.; Castro, M.; Brea, J.; Gregori-Puigjane, E.; Proenca, M. F.; Mestres, J.; Loza, M. I. Eur. J. Med. Chem. 2012, 54, 303-310.
http://dx.doi.org/10.1016/j.ejmech.2012.05.009

[27]. Santilli, A. A. Patent; American Home Products Corporation, 1981, US4266050.

[28]. Santilli, A. A.; Osdene, T. S. J. Org. Chem. 1964, 29, 2066-2068
http://dx.doi.org/10.1021/jo01030a539

[29]. Wang, K.; Kim, D.; Domling, A. J. Comb. Chem. 2010, 12, 111-118.
http://dx.doi.org/10.1021/cc9001586

[30]. Bol'but, A. V.; Kemskii, S. V.; Vovk, M. V. Russ. J. Org. Chem. 2014, 50, 685-690
http://dx.doi.org/10.1134/S107042801405011X

[31]. Santilli, A.; McCardle, L. E.; Rosenthale, M. E.; Osdene, T. S. J. Med. Chem. 1967, 10, 165-171.
http://dx.doi.org/10.1021/jm00314a008

[32]. Winkler, B.; Hueglin, D.; Eichin, K.; Ehrsam, L.; Marat, X.; Richard, H.; Kienzle, I. M.; Schroede, U. PCT Int. Appl., WO, 2013, 2013011480 A1 20130124, 10, 165.

[33]. Taunton, T.J. W.; Maglathlin, Jr. R.; Serafimova, I.; Cohen, M. S.; Miller, R.; Paavilainen, V.; McFarland, J.; Krishnan, S. US, US20130035325 A1.

[34]. Tuuttila, T.; Lipsonen, J.; Huuskonen, J.; Rissanen, K. Dyes Pigments 2008, 77, 357-362.
http://dx.doi.org/10.1016/j.dyepig.2007.06.003


How to cite


Gouda, M.; Sabah, M.; Aljuhani, W.; El-Gahani, A.; El-Enazi, S.; Al Enizi, S.; Al-Balawi, M. Eur. J. Chem. 2015, 6(2), 219-224. doi:10.5155/eurjchem.6.2.219-224.1223
Gouda, M.; Sabah, M.; Aljuhani, W.; El-Gahani, A.; El-Enazi, S.; Al Enizi, S.; Al-Balawi, M. Utility of 2-cyano-N-(2-hydroxyethyl) acetamide in heterocyclic synthesis. Eur. J. Chem. 2015, 6(2), 219-224. doi:10.5155/eurjchem.6.2.219-224.1223
Gouda, M., Sabah, M., Aljuhani, W., El-Gahani, A., El-Enazi, S., Al Enizi, S., & Al-Balawi, M. (2015). Utility of 2-cyano-N-(2-hydroxyethyl) acetamide in heterocyclic synthesis. European Journal of Chemistry, 6(2), 219-224. doi:10.5155/eurjchem.6.2.219-224.1223
Gouda, Moustafa, Meshal Abdulrahim Sabah, Waled Khaled Aljuhani, Ahmed Saleh El-Gahani, Snad Abd El-Karem El-Enazi, Salem Atalleh Al Enizi, & Majed Musallam Al-Balawi. "Utility of 2-cyano-N-(2-hydroxyethyl) acetamide in heterocyclic synthesis." European Journal of Chemistry [Online], 6.2 (2015): 219-224. Web. 29 May. 2022
Gouda, Moustafa, Sabah, Meshal, Aljuhani, Waled, El-Gahani, Ahmed, El-Enazi, Snad, Al Enizi, Salem, AND Al-Balawi, Majed. "Utility of 2-cyano-N-(2-hydroxyethyl) acetamide in heterocyclic synthesis" European Journal of Chemistry [Online], Volume 6 Number 2 (30 June 2015)

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