NAHID SHAJARI, ALI REZA KAZEMIZADEH, ALI RAMAZANI

Synthesis of 5-aryl-$N$-(trichloroacetyl)-1,3,4-oxadiazole-2-carboxamide via three-component reaction of trichloroacetyl isocyanate, ($N$-isocyanimino)triphenylphosphorane, and benzoic acid derivatives

The three-component reaction of benzoic acid derivatives, ($N$-isocyanimino)triphenylphosphorane, and trichloroacetyl isocyanate in a 1:1:1 ratio in CH$_{3}$CN occurred at room temperature, and the 5-aryl-$N$-(trichloroacetyl)-1,3,4-oxadiazole-2-carboxamide derivatives produced were formed in high yields. The reaction proceeded smoothly and cleanly under mild reaction conditions and no side reactions were observed. The structures of the products were confirmed by IR, $^{1}$H NMR, $^{13}$C NMR, mass spectroscopy, and elemental analysis.

Anahtar Kelimeler:

Multicomponent reactions, 1, 3, 4-oxadiazoles, trichloroacetyl isocyanate, ($N$-isocyanimino)triphenylphosp- horane, aza-Wittig

Synthesis of 5-aryl-N -(trichloroacetyl)-1,3,4-oxadiazole-2-carboxamide via three-component reaction of trichloroacetyl isocyanate, (N -isocyanimino)triphenylphosphorane, and benzoic acid derivatives

Keywords:

Multicomponent reactions, 1, 3, 4-oxadiazoles, trichloroacetyl isocyanate, ($N$-isocyanimino)triphenylphosp- horane, aza-Wittig,

PDF

___

1384, 1109, 832, 750, 649, 616, 439 cm −1 1H NMR (CDCl 3, 250 MHz): δ 8.52 (s, 1H, NH), 7.38–8.18 (m, 5H, arom CH) ppm. 13C NMR (CDCl 3, 9 MHz): δ 164.26 and 165.50 (2C=O), 151.54 and 153.72 (2C=N), 36, 128.49, 130.16, and 133.73 (aromatic carbons), 91.72 (CCl3) ppm. 5-(4-Methylphenyl)- N -(trichloroacetyl)-1,3,4-oxadiazole-2-carboxamide (4e)
HH= 4 Hz, 2H, arom CH), 4.56 (s, 2H, CH2 ) ppm; 13C NMR (CDCl 3, 9 MHz): δ 163.62 and 166.80 (2C=O), 152.71 and 154.62 (2C=N), 127.58 and 129.83 (4CH, arom), 123.40 and 82 (2C, arom), 92.10 (CCl3) , 32.16 (CH2Br) ppm. Zhu, J.; Bienaym´e, H. Multicomponent Reactions; Wiley-VCH: Weinheim, Germany, 2005.
Eckert, H. Molecules 2012, 17, 1074–1102.
Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Chem. Rev. 2014, 114, 8323–8359.
Nenajdenko, V. G. Isocyanide Chemistry ; Wiley-VCH: Weinheim, Germany, 2012.
D¨omling, A. Chem. Rev. 2006, 106, 17–89.
Li, Z.; Zhan, P.; Liu, X. Mini-Rev. Med. Chem. 2011, 11, 1130–1142.
Joshi, D.; Parikh, K. S. Med. Chem. Res. 2014, 23, 1855–1864.
Bondock, S.; Adel, S.; Etman, H. A.; Badria, F. A. Eur. J. Med. Chem. 2012, 48, 192–199.
Patel, R. V.; Kumari, P.; Chikhalia, K. H. Med. Chem. 2013, 9, 596–607.
Sahoo, B. M.; Dinda, S. C.; Ravi Kumar, B. V.V.; Panda, J.; Brahmkshatriya, P. S. Lett. Drug Des. Discovery 2014, 11, 82–89.
Gupta, A.; Kashaw, S. K.; Jain, N.; Rajak, H.; Soni, A.; Stables, J. P. Med. Chem. Res. 2011, 20, 1638–1642.
Saitoh, M.; Kunitomo, J.; Kimura, E.; Hayase, Y.; Kobayashi, H.; Uchiyama, N.; Kawamoto, T.; Tanaka, T.; Mol, C. D.; Dougan, D. R.; et al. Bioorg. Med. Chem. 2009, 17, 2017–2029.
Coppo, F. T.; Evans, K. A.; Graybill, T. L.; Burton, G. Tetrahedron Lett. 2004, 45, 3257–3260.
Yang, S.-J.; Lee, S.-H.; Kwak, H.-J.; Gong, Y.-D. J. Org. Chem. 2013, 78, 438–444.
Brown, B. J.; Clemens, I. R.; Neesom, J. K. Synlett 2000, 131–133.
Park, Y.-D.; Kim, J.-J.; Chung, H.-A.; Kweon, D.-H.; Cho, S.-D.; Lee, S.-G.; Yoon, Y.-J. Synthesis 2003, 560–564.
Brain, C. T.; Paul, J. M.; Loong, Y.; Oakley, P. J. Tetrahedron Lett. 1999, 40, 3275–3278.
Patel, K. N.; Jadhav, N. C.; Jagadhane, P. B.; Telvekar, V. N. Synlett 2012, 23, 1970–1972.
Oliveira, C. S.; Lira, B. F.; Barbosa-Filho, J. M.; Lorenzo, J. G. F; Athayde-Filho, P. F. Molecules 2012, 17, 10192–10231.
Katritzky, A. R.; Mohapatra, P. P.; Huang, L. Arkivoc 2008, ix, 62–68.
Adib, M.; Sheikhi, E.; Karimzadeh, M.; Bijanzadeh, H. R.; Amanlou, M. Helv. Chim. Acta 2012, 95, 788–794.
Ramazani, A.; Ahmadi, Y.; Rouhani, M.; Shajari, N.; Souldozi, A. Heteroat. Chem. 2010, 21, 368–372.
Ramazani, A.; Rouhani, M.; Rezaei, A.; Shajari, N.; Souldozi, A. Helv. Chim. Acta 2011, 94, 282–288.
Adib, M.; Sheikhi, E.; Kavoosi, A.; Bijanzadeh, H. R. Synthesis 2010, 4082–4086.
Adib, M.; Riazati Kesheh, M.; Ansari, S.; Bijanzadeh, H. R. Synlett 2009, 1575–1578.
Shajari, N.; Kazemizadeh, A. R.; Ramazani, A. J. Serb. Chem. Soc. 2012, 77, 1175–1180.
Ramazani, A.; Shajari, N.; Mahyari, A.; Ahmadi, Y. Mol. Divers. 2011, 15, 521–527.
Kazemizadeh, A. R.; Hajaliakbari, N.; Hajian, R.; Shajari, N.; Ramazani, A. Helv. Chim. Acta 2012, 94, 594–597.