Environmentally green synthesis of thioformamide derivatives

Reactions of isocyanides with thioacids in water proceeded smoothly at room temperature and in neutral conditions to afford thioformylamide and thioformamide derivatives in high yields. The reaction proceeded smoothly and cleanly under mild conditions and no side reactions were observed.

Environmentally green synthesis of thioformamide derivatives

Reactions of isocyanides with thioacids in water proceeded smoothly at room temperature and in neutral conditions to afford thioformylamide and thioformamide derivatives in high yields. The reaction proceeded smoothly and cleanly under mild conditions and no side reactions were observed.

___

  • Zhu, J.; Bienayme, H. Multicomponent Reactions. Wiley, Weinheim, 2005.
  • Henkel, B.; Sax, M.; D¨ omling, A. Tetrahedron Lett. 2003, 44, 3679–3682.
  • Waller, R. W.; Diorazio, L. J.; Taylor, B. A.; Motherwell, W. B.; Sheppard, T. D. Tetrahedron 2010, 66, 6496–6507. Yavari, I.; Hossaini, Z.; Sabbaghan, M. Mol. Divers. 2006, 10, 479–482.
  • Venkata, S. R. C.; Rao, V. R. J. Sulfur Chem. 2010, 31, 545–550.
  • Yavari, I.; Bayat, M. J.; Sirouspour, M.; Souri, S. Tetrahedron 2010, 66, 7995–7999.
  • Bayat, M.; Imanieh, H.; Zabarjad Shiraz, N.; Shah Qavidel, M. Monatsh. Chem. 2010, 141, 333–338.
  • Ramazani, A.; Nasrabadi, F. Z.; Ahmadi, Y. Helv. Chim. Acta 2011, 94, 1024–1029.
  • Ramazani, A.; Shajari, N.; Mahyari, A.; Ahmadi, Y. Mol. Divers. 2011, 15, 521–527. a) Rouhani, M.; Ramazani, A.; Joo, S. W.; Hanifehpour, Y. Bull. Korean Chem. Soc. 2012, 33, 4127–4130; b) Khoobi, M.; Ramazani, A.; Foroumad, A.; Emami, S.; Jafarpour, F.; Mahyari, A.; Slepokura, K.; Lis, T.; Shafiee, A. Helv. Chim. Acta 2012, 95, 660–671; c) Ganjali, M. R.; Aghabalazadeh, S.; Khoobi, M.; Ramazani, A.; Foroumadi, A.; Shafiee, A.; Norozi, P. Int. J. Electrochem. Sci. 2011, 6, 52–62; d) Khoobi, M.; Emami, S.; Dehghan, G.; Foroumadi, A.; Ramazani, A.; Shafiee, A. Arch. Pharm. 2011, 344, 588–594; e) Khoobi, M.; Mamani, L.; Rezazadeh, F.; Zareie, Z.; Foroumad, A.; Ramazani, A.; Shafiee, A. J. Mol. Cat. A. 2012, 359, 74–80; f) Ramazani, A.; Zeinali Nasrabadi, F.; Abdian, B.; Rouhani, M. Bull. Korean Chem. Soc. 2012, 33, 453–458; g) Zeinali Nasrabadi, F.; Ramazani, A.; Ahmadi, Y. Mol. Divers. 2011, 15, 791–798; h) Ramazani, A.; Tofangchi Mahyari, A.; Rouhani, M.; Rezaei, A. Tetrahedron Lett. 2009, 50, 5625–5627; i) Zareie, Z.; Khoobi, M.; Ramazani, A.; Foroumad, A.; Souldozi, A.; Slepokura, K.; Lis, T.; Shafiee, A. Tetrahedron 2012, 68, 6721– 6726; j) Ramazani, A.; Kazemizadeh, A. R. Curr. Org. Chem. 2011, 15, 3986–4020; k) Kazemizadeh, A. R.; Ramazani, A. Curr. Org. Chem. 2012, 16, 418–450; l) Khoobi, M.; Ramazani, A.; Foroumadi, A.; Hamadi, H.; Hojjati, Z.; Shafiee, A. J. Iran. Chem. Soc. 2011, 8, 1036–1042; m) Khoobi, M.; Foroumadi, A.; Emami, S.; Safavi, M.; Dehghan, Gh.; Alizadeh, B. H.; Ramazani, A.; Ardestani, S. K.; Shafiee, A. Chem. Biol. Drug Des. 2011, 78, 580–586; n) Ramazani, A.; Souldozi, A.; Morsali, A.; Jalilian, A. R. Z. Kristallogr. NCS 2004, 219, 247–248; o) Moosavi, R.; Abbasi, A. R.; Yousefi, M.; Ramazani, A.; Morsali, A. Ultrason. Sonochem. 2012, 19, 1221–1226; p) Ramazani, A.; Abdian, B.; Zeinali Nasrabadi, F.; Shajari, N.; Ranjdoost, Z. Bull. Korean Chem. Soc. 2012, 33, 3701–3705; q) Valizadeh Holagh, M.; Maharramov, A. M.; Allahverdiyev, M. A.; Ramazani, A.; Ahmadi, Y.; Zeinali Nasrabadi, F.; Souldozi, A. Turk. J. Chem. 2012, 36, 671–681; r) Ramazani, A.; Kalhor, R.; Rezaei, A.; Karimi, Z. Heteroat. Chem. 2012, 23, 315–321; s) Yavari, I.; Ramazani, A.; Yahya–Zadeh, A. Synth. Commun. 1996, 26, 4495–4499; t) Yavari, I.; Ramazani, A. Phosphorus Sulfur Silicon Relat. Elem. 1997, 130, 73–77; u) Ramazani, A.; Dastanra, K.; Zeinali Nasrabadi, F.; Karimi, Z.; Rouhani, M.; Hosseini, M. Turk. J. Chem 2012, 36, 467–476; v) Ramazani, A.; Azizian, A.; Bandpey, M.; Noshiranzadeh, N. Phosphorus Sulfur Silicon Relat. Elem. 2006, 181, 2731–2734; w) Ramazani, A.; Souldozi, A. Phosphorus Sulfur Silicon Relat. Elem. 2004, 179, 529–534; x) Ramazani, A.; Mahyari, A.; Farshadi, A.; Rouhani, M. Helv. Chim. Acta 2011, 94, 1831–1837; y) Massoudi, A.; Amini, I.; Ramazani, A.; Nasrabadi, F. Z.; Ahmadi, Y. Bull. Korean Chem. Soc. 2012, 33, 39–42; z) Ramazani, A.; Rezaei, A; Ahmadi, Y. Phosphorus Sulfur Silicon Relat. Elem. 2012, 187, 22–31.
  • D¨ omling, A. Chem. Rev. 2006, 106, 17–89.
  • D¨ omling, A.; Ugi, I. Angew. Chem. Int. Ed. Engl. 2000, 39, 3168–3210.
  • Ugi, I.; Werner, B.; D¨ omling, A. Molecules 2003 , 8, 53–66.
  • D¨ omling, A.; Herdtweck, E.; Heck, S. Tetrahedron Lett. 2006, 47, 1745–1747.
  • Wu, X.; Li, X.; Danishefsky, S. J. Tetrahedron Lett. 2009, 50, 1523–1525.
  • Ebert, B. M.; Ugi, I. K.; Grosche, M.; Herdtweck, E.; Herrmann, W. A. Tetrahedron 1998, 54, 11887–11898.
  • Shaabani, A.; Soleimani, E.; Rezayan, A. H. Tetrahedron Lett. 2007, 48, 6137–6140. a) Beckwith, A. L. J. In The Chemistry of Amides; Zabicky, J., Ed.; Interscience, John Wiley and Sons: New York, London, 1970, 96; b) Hurd, R. N.; DeLamater, G. Chem. Rev. 1960, 61, 45–86.
  • Jagodzinski, T. S. Chem. Rev. 2003, 103, 197–227. a) Wipf, P.; Venkatraman, S. J. Org. Chem. 1996, 61, 8004–8005; b) Attanasi, O. A.; Berretta, S.; Crescentini, L. D.; Favi, G.; Filippone, P.; Giorgi, G.; Lillini, S.; Mantellini, F. Tetrahedron Lett. 2007, 48, 2449–2451; c) Attanasi, O. A.; Crescentini, L. D.; Favi, G.; Filippone, P.; Giorgi, G.; Mantellini, F.; Perrulli, F. R.; Spinelli, D. Tetrahedron 2008, 64, 3837–3858.
  • Padwa, A.; Beall, L. S.; Heidelbaugh, T. M.; Bing, L.; Sheehan, S. M. J. Org. Chem. 2000, 65, 2684–2695.
  • McManus, S. P.; Lee, K. Y.; Pittman, C. U. J. Org. Chem. 1974, 39, 3041–3042.
  • Prokopcova, H.; Kappe, C. O. J. Org. Chem. 2007, 72, 4440–4448.
  • Kaboudin, B.; Elhamifar, D. Synthesis 2006, 224–226.
  • Ilankumaran, P.; Ramesha, A. R.; Chandrasekaran, S. Tetrahedron Lett. 1995, 36, 8311–8314.
  • Lajoie, G.; Lepine, F.; Mazaik, L.; Belleau, B. Tetrahedron Lett. 1983, 24, 3815–3818.
  • Ramazani, A.; Bodaghi, A. Tetrahedron Lett. 2000, 41, 567–568.
  • Pakravan, P.; Ramazani, A.; Noshiranzadeh, N.; Sedrpoushan, A. Phosphorus Sulfur Silicon Relat. Elem. 2007, 182, 545–549.
  • Ramazani, A.; Rahimifard, M.; Souldozi, A. Phosphorus Sulfur Silicon Relat. Elem. 2007, 182, 1–5.
  • Ramazani, A.; Rahimifard, M.; Noshiranzadeh, N.; Souldozi, A. Phosphorus Sulfur Silicon Relat. Elem. 2007, 182, 413–417. a) Ramazani, A.; Karimi, Z.; Souldozi, A.; Ahmadi, Y. Turk. J. Chem. 2012, 36, 81–91; b) Valizadeh Holagh, M.; Maharramov, A. M.; Allahverdiyev, M. A.; Ramazani, A.; Ahmadi, Y.; Souldozi, A.; Turk. J. Chem. 2012, 36, 179–188; c) Ramazani, A.; Ahmadi, Y.; Mahyari, A. Synthetic Commun. 2011, 41, 2273–2282; d) Ramazani, A.; Ahmadi, Y.; Nasrabadi, F. Z. Z. Naturforsch 2011, 66b, 184–190; e) Ramazani, A.; Rezaei, A. Org. Lett. 2010, 12, 2852–2855; f) Souldozi, A.; Ramazani, A. Arkivoc 2008, xvi, 235–242; g) Ramazani, A.; Rouhani, M.; Rezaei, A.; Shajari, N.; Souldozi, A. Helv. Chim. Acta 2011, 94, 282–288; h) Shajari, N.; Ramazani, A.; Ahmadi, Y. Bull. Chem. Soc. Ethiop. 2011, 25, 1–6; i) Ramazani, A.; Nasrabadi, F. Z.; Karimi, Z.; Rouhani, M. Bull. Korean Chem. Soc. 2011, 32, 2700–2704; j) Ramazani, A.; Farshadi, A.; Mahyari, A.; Slepokura, K.; Lis, T.; Rouhani, M. J. Chem. Crystallogr. 2011, 41, 1376–1385; k) Noshiranzadeh, N.; Ramazani, A.; ´ Slepokura, K.; Lis, T. Synth. Commun. 2008, 38 , 1560–1568; l) Ramazani, A.; Noshiranzadeh, N. Synth. Commun. 2009, 39 , 1204–1214; m) Ramazani, A.; Shajari, N.; Tofangchi Mahyari, A.; Khoobi, M.; Ahmadi, Y.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2010, 185, 2496–2502; n) Souldozi, A.; Ramazani, A.; Noshiranzadeh, N. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 587–589; o) Souldozi, A.; Ramazani, A.; Noshiranzadeh, N. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 1271–1275; p) Ramazani, A.; Amini, I.; Massoudi, A. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 2373–2376; q) Ramazani, A.; Souldozi, A. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 2189–2192; r) Ramazani, A.; Souldozi, A. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 1329–1332; s) Ramazani, A.; Souldozi, A. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 1325–1328; t) Ramazani, A.; Souldozi, A. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 2663–2666; u) Ramazani, A.; Rahimifard, M. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 2675–2678; v) Shajari, N.; Ramazani, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2010, 185, 1850–1857; w) Kazemizadeh, A. R.; Ramazani, A. Arkivoc 2008, xv, 159–165; x) Heshmati-Gonbari, M.; Ramazani, A.; Souldozi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2009, 184, 309–314; y) Ramazani, A.; Bodaghi, A. Phosphorus, Sulfur, Silicon Relat. Elem. 2004, 179, 1615–1620; z) Souldozi, A.; ´ Slepokura, K.; Lis, T.; Ramazani, A. Z. Naturforsch. 2007, 62b, 835–840.
  • Ramazani, A.; Shajari, N.; Gouranlou, F. Phosphorus Sulfur Silicon Relat. Elem. 2001, 174, 223–227.
  • Ramazani, A.; Amini, I.; Massoudi, A. Phosphorus Sulfur Silicon Relat. Elem. 2006, 181, 2225–2229. a) Souldozi, A.; Ramazani, A.; Bouslimani, N.; Welter, R. Tetrahedron Lett. 2007, 48, 2617–2620; b) Massoudi, A.; Amini, I.; Ramazani, A.; Zeinali Nasrabadi, F. Turk. J. Chem. 2012, 36, 537–544; c) Massoudi, A.; Amini, I.; Ramazani, A.; Zeinali Nasrabadi, F. Turk. J. Chem. 2012, 36, 779–787; d) Safaei-Ghomi, J.; Salimi, F.; Ramazani, A.; Zeinali Nasrabadi, F.; Ahmadi, Y. Turk. J. Chem. 2012, 36, 485–492.
  • Souldozi, A.; Ramazani, A. Tetrahedron Lett. 2007, 48, 1549–1551.
  • Souldozi, A.; Ramazani, A. Phosphorus Sulfur Silicon Relat. Elem. 2009,184, 3191–3198.
  • Souldozi, A.; Ramazani, A. Phosphorus Sulfur Silicon Relat. Elem. 2009, 184, 2344–2350.
  • Park, H. S.; Lee, I.; Kim, Y. H. Chem. Commun. 1996, 1805–1806.
  • Stockdill, J. L.; Wu, X.; Danishefsky, S. J. Tetrahedron Lett. 2009, 50, 5152–5155.
  • Li, X.; Yuan, Y.; Kan, C.; Danishefsky, S. J. J. Am. Chem. Soc. 2008, 130, 13225–13227.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Establishment of an electrochemical RNA aptamer-based biosensor to trace nanomolar concentrations of codeine

Mehdi SABERIAN, Davoud ASGARI, Yadollah OMIDI, Jaleh BARAR

Exploring distinct binding site regions of $beta_2$-adrenergic receptor via coarse-grained molecular dynamics simulations

Ebru Demet AKDO GAN, Sibel ÇAKAN

Synthesis, spectroscopic characterization, and genotoxicity of a new group of azo-oxime metal chelates

Beyza CABİR, Barış AVAR, Mehmet GÜLCAN, Ahmet KAYRALDIZ

Theoretical study on the addition reaction between propadienylidene and methyleneimine

Mengyuan WANG, Yungang CHEN, Shanshan DING, Yingde WANG

New synthetic strategy for novel 6-arylazo-5-methyl-3-aryl-thiazolo[2,3-c]- [1,2,4]triazoles and study of their solvatochromic properties

Ahmad Sami SHAWALI, Mohie Eldin Moustafa ZAYED

C2-Symmetric chiral diamine ligands for enantiomeric recognition of amino acid esters and mandelic acid by proton NMR titration method

Hayriye ARAL, Tarık ARAL, Mehmet ÇOLAK, Berrin ZİYADANOĞULLARI, Recep ZİYADANOĞULLARI

A phthalocyanine - fluorescein conjugate

Vefa AHSEN, Yunus ZORLU, İlker ÜN, Fabienne DUMOULIN, Hanife İBİŞ O ĞLU

Flavonoid constituents of Sideritis caesarea

Belkıs HALFON, Ece ÇİFTÇİ, Gülaçtı TOPÇU

A two-component protocol for synthesis of 3-(2-(substituted phenylamino)thiazol-4-yl)-2H-chromen-2-ones

Aamer SAEED, Mubeen ARIF, Madiha IRFAN, Michael BOLTE

Spectral, electrochemical, luminescence, and dye-sensitized solar cell studies of mono and d-f hetero binuclear cryptates

Arunachalam VIJAYARAJ, Raju PRABU, Ranganathan SURESH, Subbaiah MANOHARAN