Synthesis 2020; 52(11): 1707-1718
DOI: 10.1055/s-0037-1610755
paper
© Georg Thieme Verlag Stuttgart · New York

Fast and Efficient Green Procedure for the Synthesis of Benzo[5,6]chromene Derivatives and Their Sulfur Analogues in Water by Organocatalyst Potassium Phthalimide-N-oxyl

Nasser Etivand
a  Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia 5756151818, Iran   Email: n.etivand41@gmail.com   Email: n.etivand@urmia.ac.ir
,
Jabbar Khalafy
a  Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia 5756151818, Iran   Email: n.etivand41@gmail.com   Email: n.etivand@urmia.ac.ir
,
Mohammad G. Dekamin
b  Pharmaceutical and Heterocyclic Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran
› Author Affiliations
We are grateful for the financial support from Urmia University. We are also grateful for the partial financial support from The Research Council of Iran University of Science and Technology (IUST), Tehran, Iran (Grant No 160/19108).
Further Information

Publication History

Received: 26 December 2019

Accepted after revision: 10 February 2020

Publication Date:
02 March 2020 (online)


Abstract

A simple, clean, straightforward, and environmentally benign one-pot, three-component reaction of various arylglyoxal monohydrates, β-naphthol, and barbituric acid [pyrimidine-2,4,6(1H,3H,5H)-trione] or thiobarbituric acid in the presence of catalytic amounts potassium phthalimide-N-oxyl (PPINO), as a mild and efficient organocatalyst in aqueous media under reflux conditions is reported. This transformation produced the novel diverse-substituted 12-benzoyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-diones and their sulfur analogues in 82–93% yield via filtration and without utilization of any chromatography. The high yields of products, very simple operation, easy workup, availability of starting materials, green process, and high atom-economy are the main benefits of this synthetic strategy.

Supporting Information

 
  • References

    • 1a Ziyaei Halimehjani A, Hosseinkhany S. Synthesis 2015; 47: 3147
    • 1b Che F, Fu Z, Shen T, Lin Y, Song Q. Synthesis 2015; 47: 3403
    • 1c Qu F, Hu RF, Gao L, Wu J, Cheng XH, Wang S, He P. Synthesis 2015; 47: 3701
    • 1d Parikh N, Roy SR, Seth K, Kumar A, Chakraborti AK. Synthesis 2016; 48: 547
    • 1e Chauhan N, Pradhan S, Ghorai MK. J. Org. Chem. 2018; 84: 1757
    • 1f Dömling A. Chem. Rev. 2006; 106: 17
  • 2 Dekamin MG, Eslami M, Maleki A. Tetrahedron 2013; 69: 1074
    • 4a Laursen JB, Neilsen J. Chem. Rev. 2004; 104: 1663
    • 4b Wang SL, Wu FY, Cheng C, Zhang G, Liu YP, Jiang B, Shi F, Tu SJ. ACS Comb. Sci. 2011; 13: 135
  • 5 Panche AN, Diwan AD, Chandra SR. J. Nutr. Sci. 2016; 5: 1
    • 6a Dong Z, Liu X, Feng J, Wang M, Lin L, Feng X. Eur. J. Org. Chem. 2011; 137
    • 6b Moafi L, Ahadi S, Bazgir A. Tetrahedron Lett. 2010; 51: 6270
  • 7 Shanthi G, Perumal PT, Rao U, Sehgal PK. Indian J. Chem. 2009; 48: 1319
  • 8 Santhisudha S, Sreekanth T, Murali S, Kumar BV, Devi MA, Reddy CS. Cardiovasc. Hematol. Agents Med. Chem. 2016; 14: 167
    • 9a Fouda AM. Med. Chem. Res. 2016; 25: 1229
    • 9b Saffari Z, Aryapour H, Akbarzadeh A, Foroumadi A, Jafari N, Zarabi MF, Farhangi A. Tumour Biol. 2014; 35: 5845
    • 10a Kidwai M, Saxena S, Khan MK. R, Thukral SS. Bioorg. Med. Chem. Lett. 2005; 15: 4295
    • 10b Sabry NM, Mohamed HM, Khattab ES. A. E. H, Motlaq SS, El-Agrody AM. Eur. J. Med. Chem. 2011; 46: 765
  • 11 Martínez-Grau A, Marco J. Bioorg. Med. Chem. Lett. 1997; 7: 3165
  • 12 Alvey L, Prado S, Saint-Joanis B, Michel S, Koch M, Cole ST, Tillequin F, Janin YL. Eur. J. Med. Chem. 2009; 44: 2497
  • 13 Soni R, Durgapal SD, Soman SS, Georrge JJ. Arabian J. Chem. 2016; 12: 701
  • 14 Coudert P, Couquelet JM, Bastide J, Marion Y, Fialip J. Ann. Pharm. Fr. 1988; 46: 91
  • 15 Bonsignore L, Loy G, Secci D, Calignano A. Eur. J. Med. Chem. 1993; 28: 517
  • 16 Smith CW, Bailey JM, Billingham ME, Chandrasekhar S, Dell CP, Harvey AK, Hicks CA, Kingston AE, Wishart GN. Bioorg. Med. Chem. Lett. 1995; 5: 2783
  • 17 Biot C, Glorian G, Maciejewski LA, Brocard JS, Domarle O, Blampain G, Millet P, Georges AJ, Abessolo H, Dive D, Lebibi J. J. Med. Chem. 1997; 40: 3715
  • 18 Kiyani H, Ghorbani F. Res. Chem. Intermed. 2015; 41: 4031
  • 19 Reynolds GA, Drexhage KH. Opt. Commun. 1975; 13: 222
  • 20 Hafez EA. A, Elnagdi MH, Elagamey AG. A, El-Taweel FM. A. A. Heterocycles 1987; 26: 903
    • 21a Tahmassebi D, Blevins JE, Gerardot SS. Appl. Organomet. Chem. 2019; 33: e4807
    • 21b Mayank, Kaur Billing B, Agnihotri PK, Kaur N, Singh N, Jang DO. ACS Sustainable Chem. Eng. 2018; 6: 3714
  • 22 Kiyani H, Ghorbani F. Res. Chem. Intermed. 2015; 41: 7847
  • 23 Rao HS. P, Geetha K, Kamalraj M. Tetrahedron 2011; 67: 8146
  • 24 Bhattacharjee S, Das DK, Khan AT. Synthesis 2014; 46: 73
  • 25 Olyaei A, Alidoust MG. Synth. Commun. 2015; 45: 94
  • 26 Kazemi-Rad R, Azizian J, Kefayati H. Tetrahedron Lett. 2014; 55: 6887
  • 27 Brahmachari G, Nayek N. ACS Omega 2017; 2: 5025
  • 28 Mamaghani M, Nia RH, Tavakoli F, Jahanshahi P. Curr. Org. Chem. 2018; 22: 1704
  • 29 Jin TS, Xiao JC, Wang SJ, Li TS, Song XR. Synlett 2003; 2001
  • 30 Al-Matar M, Khalil KD, Meier H, Kolshorn H, Elnagdi MH. ARKIVOC 2008; (xvi): 288
  • 31 Shi YL, Shi M. Org. Lett. 2005; 7: 3057
  • 32 Khurana MJ, Nand B, Saluja P. Tetrahedron 2010; 66: 5637
  • 33 Ballini R, Bigi F, Conforti ML, Santis DD, Maggi R, Oppici G, Sartori G. Catal. Today 2000; 60: 305
    • 34a Raghuvanshi DS, Singh KN. ARKIVOC 2010; (x): 305
  • 35 Kidwai M, Saxena S, Rahman Khan MK, Thukral SS. Bioorg. Med. Chem. Lett. 2005; 15: 4295
  • 36 Naimi-jamal MR, Mashkouri S, Sharifi A. Mol. Divers. 2010; 14: 473
  • 37 Zhou Z, Yang F, Wu L, Zhang A. Chem. Sci. Trans. 2012; 1: 57
  • 38 Kumar D, Reddy VB, Mishra GB, Rann RK, Nadagouda MN, Varma RS. Tetrahedron 2007; 63: 3093
  • 39 Surpur MP, Kshirsagar S, Samant S. Tetrahedron Lett. 2009; 50: 719
  • 40 Kumar BS, Shrinvasulu N, Udupi RH, Rajitha B, Reddy YT, Reddy PN, Kumar PS. J. Heterocycl. Chem. 2006; 43: 1691
  • 41 Fan J, Wang Z. Chem. Commun. 2008; 5381
  • 42 Tulichala RP, Shankar M, Swamy KK. J. Org. Chem. 2017; 82: 5068
  • 43 Zhou JF, Tu SJ, Gao Y, Ji M. Chin. J. Org. Chem. 2001; 21: 742
  • 44 Peng Y, Song G. Catal. Commun. 2007; 8: 111
  • 45 Kemnitzer W, Kasibhatla S, Jiang S, Zhang H, Zhao J, Jia S, Xu L, Crogan-Grundy C, Denis R, Barriault N, Vaillancourt L, Charron S, Dodd J, Attardo G, Labrecque D, Lamothe S, Gourdeau H, Tseng B, Drewe J, Cai SX. Bioorg. Med. Chem. Lett. 2005; 15: 4745
    • 46a Dekamin MG, Yazdaninia N, Mokhtari J, Naimi-Jamal MR. J. Iran. Chem. Soc. 2011; 8: 537
    • 46b Dekamin MG, Javanshir S, Naimi-Jamal MR, Hekmatshoar R, Mokhtari J. J. Mol. Catal. A: Chem. 2008; 283: 29
    • 46c Dekamin MG, Varmira K, Farahmand M, Sagheb-Asl S, Karimi Z. Catal. Commun. 2010; 12: 226
    • 47a Parik N, Roy SR, Seth K, Kumar A, Chakraborti AK. Synthesis 2016; 48: 547
    • 47b Chanda A, Fokin VV. Chem. Rev. 2009; 109: 725
    • 47c Breslow R. Acc. Chem. Res. 1991; 24: 159
    • 48a Khalafy J, Etivand N, Dilmaghani S, Ezzati M, Marjani AP. A. Tetrahedron Lett. 2014; 55: 3781
    • 48b Etivand N, Khalafy J, Marjani AP. Res. Chem. Intermed. 2019; 45: 3379
    • 48c Khalafy J, Etivand N, Poursattar Marjani A, Khalillou N. J. Heterocycl. Chem. 2019; 56: 1857
    • 48d Etivand N, Sabegh MA, Khalafy J. Monatsh. Chem. 2019; 150: 317
    • 48e Ahmadi Sabegh M, Khalafy J, Etivand N. J. Heterocycl. Chem. 2018; 55: 2610
    • 48f Khalafy J, Etivand N, Khalillou N. J. Heterocycl. Chem. 2018; 24: 297
    • 48g Aslanpanjeh M, Marjani AP, Khalafy J, Etivand N. Res. Chem. Intermed. 2020; 46: 165
  • 49 Eftekhari-Sis B, Zirak M, Akbari A. Chem. Rev. 2013; 113: 2958
  • 50 Riley HA, Gray AR. Org. Synth., Coll. Vol. II. Wiley; New York: 1943: 509
  • 51 Dekamin MG, Moghaddam FM, Saeidian H, Mallakpour S. Monatsh. Chem. 2006; 137: 1591