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-00000084.xml
Synthesis 2018; 50(10): 2041-2057
DOI: 10.1055/s-0037-1609342
DOI: 10.1055/s-0037-1609342
paper
Latent Brønsted Base Solvent-Assisted Amide Formation from Amines and Acid Chlorides
This work was supported financially by the University of Tokyo. All authors acknowledge this support.Further Information
Publication History
Received: 19 January 2018
Accepted after revision: 20 February 2018
Publication Date:
20 March 2018 (online)
Abstract
Weakly basic amines, including even neutral amines such as nitroaniline and aminocarboxylic acids, react with acid chlorides very efficiently in N,N-dimethylacetamide (DMAC), without addition of a base, to give the corresponding amides in high yields. The role of DMAC and related solvents as latent Brønsted bases was studied in these amidation reactions. Less basic amines, such as aromatic amines, reacted with benzoyl chloride faster than more basic aliphatic amines.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609342.
- Supporting Information
-
References
- 1a Schneider N. Lowe DM. Sayle RA. Tarselli MA. Landrum GA. J. Med. Chem. 2016; 59: 4385
- 1b Brown DG. Boström JJ. Med. Chem. 2016; 59: 4443
- 2a Valeur E. Bradley M. Chem. Soc. Rev. 2009; 38: 606
- 2b Pattabiraman VR. Bode JW. Nature 2011; 480 (7378): 471
- 2c Saxon E. Armstrong JI. Bertozzi CR. Org. Lett. 2000; 2: 2141
- 2d Wilson RM. Stockdill JL. Wu X. Li X. Vadola PA. Park PK. Wang P. Danishefsky SJ. Angew. Chem. Int. Ed. 2012; 51: 2834
- 3a Frederick W. Raymond K. J. Am. Chem. Soc. 1980; 102: 2289
- 3b Belser P. Von Zelewsky A. Frank M. Seel C. Voegtle F. De Cola L. Barigelletti F. Balzani V. J. Am. Chem. Soc. 1993; 115: 4076
- 3c Belser P. Dux R. Baak M. Cola L. De Balzani V. Angew. Chem., Int. Ed. Engl. 1995; 34: 595
- 3d Watanabe S. Ikishima S. Matsuo T. Yoshida K. J. Am. Chem. Soc. 2001; 123: 8402
- 3e Ferraris D. Ko Y.-S. Pahutski T. Ficco RP. Serdyuk L. Alemu C. Bradford C. Chiou T. Hoover R. Huang S. Lautar S. Liang S. Lin Q. Lu MX.-C. Mooney M. Morgan L. Qian Y. Tran S. Williams LR. Wu QY. Zhang J. Zou Y. Kalish V. J. Med. Chem. 2003; 46: 3138
- 3f Ben-Haida A. Hodge P. Colquhoun HM. Macromolecules 2005; 38: 722
- 3g Kazuhisa Ishimoto K. Fukuda N. Nagata T. Sawai Y. Ikemoto T. Org. Process Res. Dev. 2014; 18: 122
- 3h Xin P. Zhu P. Su P. Hou J.-L. Li Z.-T. J. Am. Chem. Soc. 2014; 136: 13078
- 4a Kuz’min NI. Kabanova NI. Zhizdyuk BI. Chegolya AS. J. Org. Chem. USSR (English Translation) 1981; 17: 2139
- 4b Temple C. Bennett L. Rose J. Elliott R. Montgomery J. Mangum J. J. Med. Chem. 1982; 25: 161
- 4c Yoshida K. Okugawa T. Nagamtsu E. Yamashita Y. Matsuoka M. J. Chem. Soc., Perkin Trans. 1 1984; 529
- 4d Caperelli CA. Conigliaro J. J. Med. Chem. 1986; 29: 2117
- 4e Tamura N. Matsushita Y. Yoshioka K. Ochiai M. Tetrahedron 1988; 44: 3231
- 4f Hulinská H. Polívka Z. Jílek J. Šindelář K. Holubek J. Svátek E. Matoušová O. Buděšínský M. Frycová H. Protiva M. Coll. Czech. Chem. Commun. 1988; 53: 1820
- 4g Tamura M. Kawano Y. Chem. Pharm. Bull. 1990; 38: 116
- 4h Yakovlev YuYu. Nurmukhametov RN. Barashkov NN. Klimenko VG. Russ. J. Phys. Chem. 1991; 65: 110
- 4i Bigham EC. Mallory WR. Hodson SJ. Duch DS. Ferone R. Smith GK. Heterocycles 1993; 35: 1289
- 4j Pillai KM. R. Diamantidis G. Duncan L. Ranganathan RS. J. Org. Chem. 1994; 59: 1344
- 4k Raymond J. Cvetovich RJ. DiMichele L. Org. Process Res. Dev. 2006; 10: 944
- 4l Yamaoka N. Kodama H. Izuhara Y. Miyata T. Meguro K. Chem. Pharm. Bull. 2011; 59: 215
- 4m Mori Y. Iwamoto M. Mori K. Yoshida M. Honda T. Nagayama T. Nishi T. Heterocycles 2014; 89: 1413
- 4n Sato K. Takahagi H. Yoshikawa T. Morimoto S. Takai T. Hidaka K. Kamaura M. Kubo O. Adachi R. Ishii T. Maki T. Mochida T. Takekawa S. Nakakariya M. Amano N. Kitazaki T. J. Med. Chem. 2015; 58: 3892
- 5a Tso W.-W. Snyder CH. Powell HB. J. Org. Chem. 1970; 35: 849
- 5b Benedetti IE. Di Blasio B. Baine P. J. Chem. Soc., Perkin Trans. 2 1980; 500
- 5c Arnett EM. Quantitative Comparisons of Weak Organic Bases . In Progress in Physical Organic Chemistry . Vol. 1. Cohen SG. Streitwieser A. Taft RW. Wiley-Interscience Publishers; New York: 1963: 223
- 6 Brady WT. Lloyd RM. J. Org. Chem. 1980; 45: 2025
- 7a Dean JA. Lange’s Handbook of Chemistry . 15th ed. McGraw-Hill; New York: 1999
- 7b Cox BG. Acids and Bases, Solvent Effects on Acid-Base Strength . Oxford University Press; Oxford: 2013
- 8 Perron V. Abbott S. Moreau N. Lee D. Penney C. Zacharie B. Synthesis 2009; 283
Selected examples:
Selected examples: