Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00032269.xml
CC BY-NC-ND 4.0 · SynOpen 2021; 05(04): 301-307
DOI: 10.1055/a-1656-7293
DOI: 10.1055/a-1656-7293
paper
Trichloroacetimidate-Triggered Expeditious and Novel Synthesis of N-Acylbenzotriazoles
The author sincerely thanks the Council of Scientific and Industrial Research (CSIR), New Delhi (Grant Number 02(0345)/19/EMR-II) and Banaras Hindu University (IoE grant) for funding. MSY and MKJ acknowledge the Council of Scientific and Industrial Research (CSIR) for SRF Fellowships and SK for a Junior Research Fellowship. The authors also thank CISC-Banaras Hindu University, Varanasi.
This manuscript is dedicated to Prof. (em). Richard R. Schmidt for his notable contribution on imidate chemistry
Abstract
A facile route for the synthesis of a diverse range of N-acylbenzotriazole derivatives from the corresponding carboxylic acids has been established through a carbonyl activation pathway. In this method, trichloroacetonitrile is performed as an effective reagent for an easy access of N-acylbenzotriazoles which was simply proceeded through the activation of carboxylic acids via in situ imidate formation in anhydrous 1,2-dichloroethane followed by addition of 1H-benzotriazole at 80 °C for 3–4 h. Easy handling, one-pot, and metal-free conditions demonstrate the notable merits of the devised protocol.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1656-7293. Included are copies of 1H and 13C NMR for all the synthesized ureas and their derivatives and thiocarbamates for this article.
- Supporting Information
Publication History
Received: 12 September 2021
Accepted after revision: 27 September 2021
Accepted Manuscript online:
28 September 2021
Article published online:
13 October 2021
© 2021. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Katritzky AR, Lan X, Yang JZ, Denisko OV. Chem. Rev. 1998; 98: 409
- 2 Briguglio I, Piras S, Corona P, Gavini E, Nieddu M, Boatto G, Carta A. Eur. J. Med. Chem. 2015; 97: 612
- 3 Katritzky AR, Rachwal S. Chem. Rev. 2010; 110: 1564
- 4a Kale RR, Prasad V, Mohapatra PP, Tiwari VK. Monatsh. Chem. 2010; 141: 1159
- 4b Yu J, Singh AS, Yan G, Yu J, Tiwari VK. Synthesis 2020; 52: 3781
- 5 Singh M, Singh AS, Mishra N, Agrahari AK, Tiwari VK. ACS Omega 2019; 4: 2418
- 6a Katritzky AR, Rogovoy BV, Kirichenko N, Vvedensky V. Bioorg. Med. Chem. Lett. 2002; 12: 1809
- 6b Katritzky AR, Suzuki K, Singh SK, He H.-Y. J. Org. Chem. 2003; 68: 5720
- 6c Katritzky AR, Singh SK, Cai C, Bobrov S. J. Org. Chem. 2006; 71: 3364
- 6d Kale RR, Prasad V, Tiwari VK. Lett. Org. Chem. 2010; 7: 136
- 7a Zhou G, Lim D, Fang F, Coltart DM. Synthesis 2009; 3350
- 7b Xia Z, Lv X, Wang W, Wang X. Tetrahedron Lett. 2011; 52: 4906
- 7c Katritzky AR, Shestopalov AA, Suzuki K. Synthesis 2004; 1806
- 8 Katritzky AR, Widyan K, Kirichenko K. J. Org. Chem. 2007; 72: 5802
- 9 Gonnet Lori, Tintillier T, Venturini N, Konnert L, Hernandez J.-F, Lamaty F, Laconde G, Martinez J, Colacino E. ACS Sustainable Chem. Eng. 2017; 5: 2936
- 10a Wang X, Zhang Y. Synth. Commun. 2003; 33: 2627
- 10b Lim D, Fang F, Zhou G, Coltart DM. Org. Lett. 2007; 9: 4139
- 11 Katritzky AR, Abdel-Fattah AA. A, Wang M. J. Org. Chem. 2003; 68: 4932
- 12 Katritzky AR, Abdel-Fattah AA. A, Wang M. J. Org. Chem. 2003; 68: 1443
- 13 Katritzky AR, Cai C, Suzuki K, Singh SK. J. Org. Chem. 2004; 69: 811
- 14a Wang X, Wang W, Wen Y, He L, Zhu X. Synthesis 2008; 3223
- 14b Katritzky AR, Suzuki K, Wang Z. Synlett 2005; 1656
- 14c Li J, Sun Y, Chen Z, Su W. Synth. Commun. 2010; 40: 3669
- 15 Singh AS, Kumar D, Mishra N, Tiwari VK. ChemistrySelect 2017; 2 224
- 16 Singh AS, Mishra N, Kumar D, Tiwari VK. ACS Omega 2017; 2: 5044
- 17a Yadav MS, Singh AS, Agrahari AK, Mishra N, Tiwari VK. ACS Omega 2019; 4: 6681
- 17b Kumar D, Mishra BB, Tiwari VK. J. Org. Chem. 2014; 79: 251
- 17c Kumar D, Mishra A, Mishra BB, Bhattacharya S, Tiwari VK. J. Org. Chem. 2013; 78: 899
- 17d Singh AS, Kumar D, Tiwari VK. ChemistrySelect 2018; 3: 7809
- 17e Singh AS, Mishra N, Yadav MS, Tiwari VK. J. Heterocycl. Chem. 2019; 56: 275
- 18a Yadav MS, Singh SK, Agrahari AK, Singh AS, Tiwari VK. Synthesis 2021; 53: 2494
- 18b Singh AS, Kumar D, Mishra N, Tiwari VK. RSC Adv. 2016; 6: 84512
- 18c Singh AS, Agrahari AK, Singh SK, Yadav MS, Tiwari VK. Synthesis 2019; 51: 3443
- 20 Agha KA, Abo-Dya NE, Ibrahim TS, Abdel-Aal EH. ARKIVOC 2016; (iii): 161
- 21 Singh M, Agrahari AK, Mishra N, Singh AS, Tiwari VK. Ind. J. Heterocycl. Chem. 2018; 28: 125
- 22 Duangkamol C, Wangngae S, Pattarawarapan M, Phakhodee W. Eur. J. Org. Chem. 2014; 7109
- 23 Kanışkan N, Kökten S, Celik I. ARKIVOC 2012; (viii): 198
- 24 Wet-osot S, Duangkamol C, Pattarawarapan M, Phakhodee W. Monatsh. Chem. 2015; 146: 959
- 25a Katritzky AR, Shobana N, Pernak J, Afridi AS, Fan WQ. Tetrahedron 1992; 48: 7817
- 25b Katritzky AR, Zhang Y, Singh SK. Synthesis 2003; 2795
- 26 Singh AS, Agrahari AK, Mishra N, Singh M, Tiwari VK. Synthesis 2019; 51: 470
- 27 Singh M, Singh AS, Mishra N, Agrahari AK, Tiwari VK. Synthesis 2019; 51: 2183
- 28 Jang DO, Park DJ, Kim J. Tetrahedron Lett. 1999; 5323
- 29 Prusinowski AF, Twumasi RK, Wappes EA, Nagib DA. J. Am. Chem. Soc. 2020; 142: 5429
- 30 Tanaka R, Tanimoto I, Kojima M, Yoshino T, Matsunaga S. J. Org. Chem. 2019; 84: 13203
- 31 Mezailles N, Ricard L, Gagosz F. Org. Lett. 2005; 7: 4133
- 32 Gayakhe V, Ardhapure AK, Kapdi AR, Sanghvi YS, Serrano JL, García L, Pérez J, García J, Sánchez G, Fischer C, Schulzke C. J. Org. Chem. 2016; 81: 2713
- 33 Agrahari AK, Bose P, Jaiswal MK, Rajkhowa S, Singh AS, Hotha S, Mishra N, Tiwari VK. Chem. Rev. 2021; 12: 7638
- 34 Tiwari VK, Mishra BB, Mishra KB, Mishra N, Singh AS, Chen X. Chem. Rev. 2016; 116: 3086
- 35 Agrahari AK, Jaiswal MK, Yadav MS, Tiwari VK. Carbohydr. Res. 2021; 508: 108403
- 36 Agrahari AK, Singh AS, Mukharjee RK, Tiwari VK. RSC Adv. 2020; 43: 31553
- 37 Schmidt RR, Michel J. Angew. Chem., Int. Ed. Engl. 1980; 19: 731
- 38a Schmidt RR, Michel J. J. Carbohydr. Chem. 1985; 4: 141
- 38b Schmidt RR, Kinzy W. Adv. Carbohydr. Chem. Biochem. 1994; 50: 21
- 39 Maharani NS, Meador RI. L, Smith TJ, Canarelli SE, Adhikari AA, Shah JP, Russo CM, Wallach DR, Howard KT, Millimaci AM, Chisholm JD. J. Org. Chem. 2019; 84: 7871
- 40 Betori RC, Miller ER, Scheidt KA. Adv. Synth. Catal. 2017; 359: 1131
- 41 Katritzky AR, Cai C, Singh SK. J. Org. Chem. 2006; 71: 3375
- 42 Wet-osot S, Phakhodee W, Pattarawarapan M. Tetrahedron Lett. 2015; 56: 6998
- 43 Matilde CV, Nagel Heinze T. Polym. Bull. 2010; 65: 873
- 44 Pocquet L, Vologdin N, Mangiatordi GF, Ciofini I, Nicolotti O, Thorimbert S, Salmain M. Eur. J. Inorg. Chem. 2017; 3622