Abstract
A new and efficient isocyanide-based one-pot multi-component approach for the synthesis of novel spiroiminolactone derivatives is described. Products were obtained by a three-component condensation reaction of 1,3-diones, reactive cyclic carbonyl compounds, and isocyanides in the presence of a catalytic amount of tetrabutylammonium hydrogensulfate in water. Using this method, target compounds were synthesized with great efficiency and atom economy.
Graphical abstract
Similar content being viewed by others
References
Syamala M (2009) Org Prep Proced Int 41:1
Ramon DJ, Yus M (2005) Angew Chem Int Ed 44:1602
Chernyak D, Gevorgyan V (2007) J Am Chem Soc 129:9868
Waldmann H, Kuhn M, Liu W, Kumar K (2008) Chem Commun 1211
de Meijere A, von Zezschwitz P, Bräse S (2005) Acc Chem Res 38:413
Tietze FL, Brasche G, Gericke K (2006) Domino reactions in organic synthesis. Wiley-VCH, Germany
Shaabani A, Maleki A, Rezayan HA, Sarvary A (2011) Mol Divers 15:41
Heravi MM, Moghimi S (2011) J Iran Chem Soc 8:306
Shapiro N, Vigalok A (2008) Angew Chem 120:2891
Narayan S, Muldoon J, Finn MG, Fokin VV, Kolb HC, Sharpless KB (2005) Angew Chem 117:3339
Price BK, Tour JM (2006) J Am Chem Soc 128:12899
Shaabani A, Hajishaabanha F, Mofakham H, Mahyari M, Lali B (2012) Helv Chim Acta 95:246
Adib M, Mahdavi M, Bagherzadeh S, Zhu LG, Rahimi-Nasrabadi M (2010) Tetrahedron Lett 51:27
Kerton FM (2009) Alternative solvents for green chemistry. Royal Society of Chemistry, Cambridge
Sundberg JR (1996) The chemistry of indoles. Academic, New York
Da-Silva MJF, Garden JS, Pinto CA (2001) J Braz Chem Soc 12:273
Joshi CK, Jain R, Sharma JK (1988) Indian Chem Soc 115:202
Abdel-Rahman AH, Keshk ME, Hanna AM, El-Bady MS (2004) Bioorg Med Chem 12:2483
Ghahremanzadeh R, Sayyafi M, Ahadi S, Bazgir A (2009) J Comb Chem 11:393
Chen BW, Wu JZ, Pei LQ, Cun FL, Zhang MX, Yuan CW (2010) Org Lett 12:3132
Chen T, Xu PX, Ji JS (2010) J Comb Chem 12:659
Schulz V, Davoust M, Lemarie M, Lohier FJ, De Oliveira Santos JS, Metzner P, Briere FJ (2007) Org Lett 9:1745
Majumdar KC, Ponra S, Nandi RK (2012) Tetrahedron Lett 53:1732
Ahadi S, Abaszadeh M, Bazgir A (2012) Mol Divers 16:299
White JD, Li Y, Ihle DC (2010) J Org Chem 75:3569
Khafagy MM, El-Wahas AHFA, Eid FA, El-Agrody AM (2002) Farmaco 57:715
Sebahar PR, Williams RM (2000) J Am Chem Soc 122:5666
Kang TH, Matsumoto K, Murakami Y, Takayama H, Kitajima M, Aimi N, Watanabe H (2002) Eur J Pharmacol 444:39
Dabiri M, Bahramnejad M, Baghbanzadeh M (2009) Tetrahedron 65:9443
Jadidi K, Ghahremanzadeh R, Bazgir A (2009) J Comb Chem 11:341
Liu H, Dou G, Shi D (2010) J Comb Chem 12:292
Ghahremanzadeh R, Imani-Shakibaei G, Ahadi S, Bazgir A (2010) J Comb Chem 12:191
Nair V, Vellalath S, Poonoth M, Mohan R, Suresh E (2006) Org Lett 8:507
Elinson MN, Ilovaisky AI, Dorofeev AS, Merkulova VM, Stepanov NO, Miloserdov FM, Ogibin YN, Nikishin GI (2007) Tetrahedron 63:10543
Sun J, Sun Y, Gao H, Yan CG (2012) Eur J Org Chem 1976
Li J, Liu Y, Li C, Jiea H, Jia X (2012) Green Chem 14:1314
Ahadi S, Khavasi HR, Bazgir A (2008) Chem Pharm Bull 56:1328
Liang B, Kalidindi S, Porco JA, Stephenson CRJ (2010) Org Lett 12:572
Esmaeili A, Bodaghi A (2003) Tetrahedron 59:1169
Yavari I, Mokhtarporyani-Sanandaj A, Moradi L, Mirzaei A (2008) Tetrahedron 64:5221
Maghsoodlou MT, Hazeri N, Habibi-Khorassani SM, Marandi G, Nassiri M (2006) J Heterocycl Chem 43:481
Ramazani A, Rezaei A, Tofangchi-Mahyari A, Rouhani M, Khoobi M (2010) Helv Chim Acta 93:2033
Esmaeili AA, Darbanian M (2003) Tetrahedron 59:5545
Safaei HR, Shekouhy M, Shirinfeshan A, Rahmanpoor S (2012) Mol Divers 16:669
Safaei HR, Shekouhy M, Rahmanpoor S, Shirinfeshan A (2012) Green Chem 14:1696
Butler RN, Coyne AG (2010) Chem Rev 110:6302
Acknowledgments
We are grateful to the Islamic Azad University (Shiraz Branch) Research Councils for the financial support of this work. We also thank Dr. M. M. Ghanbari, faculty member of the Islamic Azad University (Sarvestan Branch), for his useful advice.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Safaei, H.R., Shioukhi, N. & Shekouhy, M. Isocyanide-based one-pot three-component synthesis of novel spiroiminolactone derivatives in water. Monatsh Chem 144, 1855–1863 (2013). https://doi.org/10.1007/s00706-013-1060-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-013-1060-1