Citation: Mohebat Razieh, Yazdani-Elah-Abadi Afshin, Maghsoodlou Malek-Taher, Hazeri Nourallah. DABCO-catalyzed multi-component domino reactions for green and efficient synthesis of novel 3-oxo-3H-benzo[a]pyrano[2, 3-c] phenazine-1-carboxylate and 3-(5-hydroxybenzo[a]phenazin-6-yl) acrylate derivatives in water[J]. Chinese Chemical Letters, ;2017, 28(5): 943-948. doi: 10.1016/j.cclet.2016.12.042 shu

DABCO-catalyzed multi-component domino reactions for green and efficient synthesis of novel 3-oxo-3H-benzo[a]pyrano[2, 3-c] phenazine-1-carboxylate and 3-(5-hydroxybenzo[a]phenazin-6-yl) acrylate derivatives in water

a.
Young Researchers and Elite Club, Yazd Branch, Islamic Azad University, Yazd, Iran
b.
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674, Zahedan, Iran

Corresponding author: Yazdani-Elah-Abadi Afshin, afi_yazdani@yahoo.com Maghsoodlou Malek-Taher, mt_maghsoodlou@yahoo.com; mt_maghsoodlou@chem.usb.ac.ir
Received Date: 24 October 2016
Revised Date: 29 November 2016
Accepted Date: 7 December 2016
Available Online: 8 May 2017

Figures(4)

An efficient, convenient and environmentally benign procedure for the synthesis of novel 3-oxo-3H-benzo[a]pyrano[2, 3-c]phenazine-1-carboxylate and 3-(5-hydroxybenzo[a]phenazin-6-yl)acrylate derivatives has been developed by domino three-component condensation reaction between 2-hydroxynaphthalene-1, 4-dione, benzene-1, 2-diamines and acetylenic esters in the presence of a catalytic amount of DABCO as an expedient, eco-friendly and reusable base catalyst in water. This green process produces biologically and pharmacologically significant heterocycles in a one-pot single operation and offers considerable advantages such as:operational simplicity, short reaction time, high yields, reusability of catalyst, absence of any tedious workup or purification and avoids hazardous reagents/solvents.
- Multi-component domino reactions (MDRs),
- DABCO,
- Acetylenic esters,
- Benzo[a]phenazin derivatives,
- Green chemistry
1. [1]
  Yu J., Shi F., Gong L.Z.. Brønsted-acid-catalyzed asymmetric multicomponent reactions for the facile synthesis of highly enantioenriched structurally diverse nitrogenous heterocycles[J]. Acc. Chem. Res., 2011(44):1156-1171.
2. [2]
  Singh M.S., Nandi G.C., Chanda T.. β-Oxodithioesters:a new frontier for diverse heterocyclic architectures[J]. RSC Adv., 2013(3):14183-14198.
3. [3]
  Xu Z., Ayaz M., Cappelli A.A., Hulme C.. General one-pot, two-step protocol accessing a range of novel polycyclic heterocycles with high skeletal diversity[J]. ACS Comb. Sci., 2012(14):460-464.
4. [4]
  Jiang B., Tu S.J., Kaur P., Wever W., Li G.. Four-component domino reaction leading to multifunctionalized quinazolines[J]. J. Am. Chem. Soc., 2009(131):11660-11661.
5. [5]
  Knapp J.M., Zhu J.S., Tantillo D.J., Kurth M.J.. Multicomponent assembly of highly substituted indoles by dual palladium-catalyzed coupling reactions[J]. Angew. Chem. Int. Ed., 2012(51):10588-10591.
6. [6]
  Li M., Cao H., Wang Y., Lv X.L., Wen L.R.. One-pot multicomponent cascade reaction of N S-ketene acetal:solvent-free synthesis of imidazo[1, 2-a] thiochromeno[3.2-e]pyridines[J]. Org. Lett., 2012(14):3470-3473.
7. [7]
  Khurana J.M., Chaudhary A., Lumb A., Nand B.. An expedient four-component domino protocol for the synthesis of novel benzo[a] phenazine annulated heterocycles and their photophysical studies[J]. Green Chem., 2012(14):2321-2327.
8. [8]
  McNulty J., Das P.. Highly stereoselective and general synthesis of (E)-stilbenes and alkenes by means of an aqueous Wittig reaction[J]. Eur. J. Org. Chem., 2009:4031-4035.
9. [9]
  McNulty J., Das P., McLeod D.. Microwave-assisted, aqueous wittig reactions:organic-solvent-and protecting-group-free chemoselective synthesis of functionalized alkenes[J]. Chem. Eur. J., 2010(16):6756-6760.
10. [10]
  Narayan S., Muldoon J., Finn M.G.. On water:unique reactivity of organic compounds in aqueous suspension[J]. Angew. Chem. Int. Ed., 2005(44):3275-3279.
11. [11]
  Smith M.B., March J.. March's advanced organic chemistry:reactions, mechanisms, and structure[J]. John Wiley & Sons, 2007.
12. [12]
  R. Breslow, in: M. Lindstrom (Ed. ), In Organic Reactions in Water, Blackwell, Oxford, 2007, pp. 1-28.
13. [13]
  Rideout D.C., Breslow R.. Hydrophobic acceleration of Diels-Alder reactions[J]. J. Am. Chem. Soc., 1980(102):7816-7817.
14. [14]
  Breslow R.. Hydrophobic effects on simple organic reactions in water[J]. Acc. Chem. Res., 1991(24):159-164.
15. [15]
  Dömling A., Ugi I.. Multicomponent reactions with isocyanides[J]. Angew. Chem. Int. Ed., 2000(39):3168-3210.
16. [16]
  Dömling A.. Recent developments in isocyanide based multicomponent reactions in applied chemistry[J]. Chem. Rev., 2006(106):17-89.
17. [17]
  de Witte N.V., Stoppani A.O., Dubin M.. 2-Phenyl-β-lapachone can affect mitochondrial function by redox cycling mediated oxidation[J]. Arch. Biochem. Biophys., 2004(432):129-135.
18. [18]
  Lopez L.M., Pellegrino de Iraldi A., Carrizo P.H., Dubin M., Stoppani A.O.M.. Effect of the lipophilic o-naphthoquinone CG 10-248 on rat liver mitochondria structure and function[J]. Biocell, 2002(26):237-245.
19. [19]
  Ferreira S.B., Salom K., da Silva F.C.. Synthesis and anti-trypanosoma cruzi activity of β-lapachone analogues[J]. Eur. J. Med. Chem., 2011(46):3071-3077.
20. [20]
  Bloxham J., Dell C.P., Smith C.. Preparation of some new benzylidenemalononitriles by an SNAr reaction:application to naphtho[1, 2-b] pyran synthesis[J]. Heterocycles, 1994(38):399-408.
21. [21]
  Makgatho M.E., Anderson R., sullivan J.F. O'. Tetramethylpiperidinesubstituted phenazines as novel anti-plasmodial agents[J]. Drug Develop. Res., 2000(50):195-202.
22. [22]
  de Andrade-Neto V.F., Goulart M.O., da Silva Filho J.F.. β-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo[J]. Bioorg. Med. Chem. Lett., 2004(14):1145-1149.
23. [23]
  Neves-Pinto C., Malta V., Pinto M.. A trypanocidal phenazine derived from β-lapachone[J]. J. Med. Chem., 2002(45):2112-2115.
24. [24]
  Cartwright D.K., Chilton W.S., Benson D.M.. Benson, Pyrrolnitrin and phenazine production by Pseudomonas cepacia strain 5.5 B, a biocontrol agent of Rhizoctonia solani[J]. Appl. Microbiol. Biotechnol., 1995(43):211-216.
25. [25]
  Ligon J.M., Hill D.S., Hammer P.E.. Natural products with antifungal activity from Pseudomonas biocontrol bacteria[J]. Pest. Manag. Sci., 2000(56):688-695.
26. [26]
  Muller M., Sorrell T.C.. Inhibition of the human platelet cyclooxygenase response by the naturally occurring phenazine derivative, 1-hydroxyphenazine[J]. Prostaglandins, 1995(50):301-311.
27. [27]
  Rewcastle G.W., Denny W.A., Baguley B.C.. Potential antitumor agents. 51. Synthesis and antitumor activity of substituted phenazine-1-carboxamides[J]. J. Med. Chem., 1987(30):843-851.
28. [28]
  Lee H.J., Kim J.S., Park S.Y.. Synthesis and cytotoxicity evaluation of 6, 11-dihydro-pyridazo-and 6, 11-dihydro-pyrido[2, 3-b]phenazine-6, 11-diones[J]. Bioorg. Med. Chem., 2004(12):1623-1628.
29. [29]
  Kim J.S., Rhee H.K., Park H.J.. Synthesis of 6-chloroisoquinoline-58-diones and pyrido[3, 4-b]phenazine-5, 12-diones and evaluation of their cytotoxicity and DNA topoisomerase Ⅱ inhibitory activity[J]. Bioorg. Med. Chem., 2007(15):451-457.
30. [30]
  Maghsoodlou M.T., Habibi S.M., Khorassani -, Moradi A.. One-pot threecomponent synthesis of functionalized spirolactones by means of reaction between aromatic ketones, dimethyl acetylenedicarboxylate, and Nheterocycles[J]. Tetrahedron, 2011(67):8492-8495.
31. [31]
  Dastoorani P., Maghsoodlou M.T., Khalilzadeh M.A., Sarina E.. Synthesis of new dibenzofuran derivatives via Diels-Alder reaction of euparin with activated acetylenic esters[J]. Tetrahedron Lett., 2016(57):314-316.
32. [32]
  Maghsoodlou M.T., Khorassani S.M.H., Heydari R.. Highly stereoselective construction of functionalized cyclopropanes from the reaction between acetylenic esters and C-H acids in the presence of triphenylarsine[J]. Tetrahedron Lett., 2009(50):4439-4442.
33. [33]
  Rostami Charati F., Maghsoodlou M.T., Habibi-Khorassani S.M., Makha M.. Green diastereoselective synthesis of highly functionalised trifluoromethylated γ-lactone phosphonate esters bearing a thioester or ketothiophene[J]. Tetrahedron Lett., 2008(49):343-347.
34. [34]
  Doostmohammadi R., Maghsoodlou M.T., Hazeri N., Habibi-Khorassani S.M.. Acetic acid as an efficient catalyst for the one-pot preparation of 3, 4, 5-substituted furan-2(5H)-ones[J]. Res. Chem. Intermed., 2013(39):4061-4066.
35. [35]
  Doostmohammadi R., Maghsoodlou M.T., Hazeri N., Habibi-Khoras S.M.. An efficient one-pot multi-component synthesis of 3, 4, 5-substituted furan-2(5H)-ones catalyzed by tetra-n-butylammonium bisulphate[J]. Chin. Chem. Lett., 2013(24):901-903.
36. [36]
  Sajadikhah S.S., Maghsoodlou M.T., Hazeri N.. A simple and efficient approach to one-pot synthesis of mono-and bis-N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates catalyzed by InCl₃[J]. Chin. Chem. Lett., 2014(25):58-60.
37. [37]
  Bita B.. 1, 4-Diazabicyclo[2.2.2] octane (DABCO) as a useful catalyst in organic synthesis[J]. Eur. J. Chem., 2010(1):54-60.
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