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Synthesis 2014; 46(11): 1463-1468
DOI: 10.1055/s-0033-1341101
DOI: 10.1055/s-0033-1341101
paper
Facile Direct Synthesis of Acetylenedicarboxamides
Weitere Informationen
Publikationsverlauf
Received: 13. Januar 2014
Accepted after revision: 11. Februar 2014
Publikationsdatum:
17. März 2014 (online)
Abstract
A convenient, rapid and widely applicable one-pot procedure has been developed for the synthesis of acetylenedicarboxamides from various primary and secondary amines, including amino acid derivatives, protected carbohydrates, and fluorescent labels. By using DMTMM for amide coupling, acetylenedicarboxylic acid was directly converted into acetylenedicarboxamides in highly competitive overall yields (52–80%).
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Neochoritis CG, Constantinos G, Zarganes-Tzitzikas T, Stephanidou-Stephanatou J. Synthesis 2014; 46: 537
- 1b Holmes HL In Organic Reactions . Wiley; New York: 2004: 60-173
- 1c Winterfeldt E. Angew. Chem. Int. Ed. 1967; 6: 423
- 1d Huisgen R. Angew. Chem. Int. Ed. 1963; 2: 565
- 2a Amanpour T, Mirzaei P, Bazgir A. Synthesis 2012; 44: 235
- 2b Villemin E, Marchand-Brynaert J. Synthesis 2012; 44: 1923
- 2c Wu C, Wang Q, Jingjing Z, Li P, Shi F. Synthesis 2012; 44: 3033
- 2d Bhunia N, Biswanath D. Synthesis 2013; 45: 1045
- 3a Heyl D, Rikowski E, Hoffmann RC, Schneider JJ, Fessner W.-D. Chem. Eur. J. 2010; 16: 5544
- 3b Fabritz S, Heyl D, Bagutski V, Empting M, Rikowski E, Frauendorf H, Balog I, Fessner W.-D, Schneider JJ, Avrutina O, Kolmar H. Org. Biomol. Chem. 2010; 8: 2212
- 4a Schulte KE, Reisch J, Coen K. Chim. Ther. 1970; 5: 72
- 4b Hashmi AS. K, Grundl MA, Nass AR, Naumann F, Bats JW, Bolte M. Eur. J. Org. Chem. 2001; 4705
- 5 Herkes FE, Simmons HE. J. Org. Chem. 1975; 40: 420
- 6a Diels O, Thiele WE. Ber. Dtsch. Chem. Ges. B 1938; 71: 1173
- 6b McDonald RN, Krueger RA. J. Org. Chem. 1963; 28: 2542
- 6c Maier G, Jung WA. Chem. Ber. 1982; 115: 804
- 7a Das S, Das U, Varela-Ramirez A, Lema V, Aguillera RJ, Balzarini J, De Clercq E, Dimmock SG, Gorecki DK. J, Dimmock JR. ChemMedChem 2011; 10: 2011
- 7b Das S, Das U, Sakagami H, Umemura N, Iwamoto S, Matsuta T, Kawase M, Molnar J, Serly J, Gorecki DK. J, Dimmock JR. Eur. Med. Chem. 2012; 51: 193
- 8 Maier G, Jung GA. Tetrahedron Lett. 1980; 21: 3875
- 9 Alvaro M, Garcia H, Miranda MA, Primo J. Tetrahedron 1992; 48: 3437
- 10 Paul R, Anderson GW. J. Am. Chem. Soc. 1960; 82: 4596
- 11 Eichelberger L. J. Am. Chem. Soc. 1926; 48: 1320
- 12a Han S.-Y, Kim S.-Y. Tetrahedron 2004; 60: 2447
- 12b El-Faham A, Albericio F. Chem. Rev. 2011; 111: 6557
- 12c Al-Warhi TI, Al-Hazimi HM. A, El-Faham A. J. Saudi Chem. Soc. 2012; 16: 97
- 13a Kaminski ZJ, Paneth P, Rudzinski J. J. Org. Chem. 1998; 63: 4248
- 13b Kunishima M, Kawachi C, Iwasaki F, Terao K, Tani S. Tetrahedron Lett. 1999; 40: 5327
- 14 Cronin JS, Ginah FO, Murray AR, Copp JD. Synth. Commun. 1996; 26: 3491
- 15 Kunishima M, Kawachi C, Monta J, Terao K, Iwasaki F, Tani S. Tetrahedron 1999; 55: 13159
- 16 Shieh W.-C, Chen Z, Xue S, McKenna J, Wang R.-N, Prasad K, Repic O. Tetrahedron Lett. 2008; 49: 5359
- 17 Kunishima M, Kawachi C, Hioki K, Terao K, Tani S. Tetrahedron 2001; 57: 1551
- 18 Kunishima M, Kitao A, Kawachi C, Watanabe Y, Iguchi S, Hioki K, Tani S. Chem. Pharm. Bull. 2002; 50: 549
- 19 Falchi A, Giacomeli G, Porcheddu A, Taddei M. Synlett 2000; 275
- 20 El Moncef A, Zaballos E, Zaragoza RJ. Tetrahedron 2011; 67: 3677 ; we follow the suggested terminology as there is no other consistent naming of amide conformers
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