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Article title

Diversity oriented, efficient and sustainable synthetic protocol for the synthesis of structurally diverse drug-like complex heterocycles, incorporating privileged heterocyclic systems


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A diversity oriented, efficient and sustainable
synthetic protocol has been presented for the synthesis
of structurally diverse drug-like small heterocycles
with structural complexity. The present synthetic
strategy involves a three-component domino reaction of
2-aminobenzothiazoles, thiophene-2-carbaldehyde and
carbonyl compounds in the presence of a catalytic amount
of sulfamic acid as a recyclable ecofriendly acid catalyst.







Physical description


1 - 9 - 2014
14 - 7 - 2014
19 - 9 - 2014


  • Department of Chemistry, University of Rajasthan, Jaipur, 302004, India
  • Department of Chemistry, University of Rajasthan, Jaipur, 302004, India
  • Department of Chemistry, University of Rajasthan, Jaipur, 302004, India
  • Department of Chemistry, University of Rajasthan, Jaipur, 302004, India
  • Department of Chemistry, University of Rajasthan, Jaipur, 302004, India


  • [1] Burke M.D., Schreiber S.L., A planning strategy for diversityorientedsynthesis, Angew. Chem. Int. Ed., 2004, 43, 46-58.[Crossref]
  • [2] Horton D.A., Bourne T.G., Smythe M.L., The CombinatorialSynthesis of Bicyclic Privileged Structures or PrivilegedSubstructures, Chem. Rev., 2003, 103, 893-930.[Crossref]
  • [3] Kennedy J.P., Williams L., Bridges T.M., Daniels R.N., Weaver D.,Lindsley C.W., Application of Combinatorial Chemistry Scienceon Modern Drug Discovery, J. Comb. Chem., 2008, 10(3),345-354.[Crossref][WoS]
  • [4] Tietze L.F., Domino Reactions in Organic Synthesis, Chem. Rev.,1996, 96, 115-136.
  • [5] Tietze L.F., Brasche G., Gericke K.M.; (Eds), Domino Reactionsin Organic Synthesis, Wiley-VCH Weinheim , Germany , 2006.
  • [6] Powner M.W., Sutherland J.D., Szostak J.W., ChemoselectiveMulticomponent One-Pot Assembly of Purine Precursors inWater, J. Am. Chem. Soc., 2010, 132 ,16677–16688.[WoS]
  • [7] Marigo M., Schulte T., Franzen J., Jørgensen K.A., Asymmetricmulticomponent domino reactions and highly enantioselectiveconjugated addition of thiols to alpha,beta-unsaturatedaldehydes, J. Am. Chem. Soc., 2005, 127, 15710-15711.[Crossref]
  • [8] Neumann H., Wangelin A.J.V., Gordes, D., Spannenberg A.,Beller M., A New Multicomponent Coupling of Aldehydes,Amides, and Dienophiles: Atom-Efficient One-Pot Synthesis ofHighly Substituted Cyclohexenes and Cyclohexadienes, J. Am.Chem. Soc., 2001, 123(34), 8398-8399.
  • [9] Chen X.H., Xu X.Y., Liu H., Cun L.F., Gong L.Z., Highly EnantioselectiveOrganocatalytic Biginelli Reaction, J. Am. Chem Soc.,2006, 128, 14802-14803.[Crossref]
  • [10] Jiang B., Tu S.J., Kaur P., Wever W., Li G., J. Am. Chem. Soc.,2009, 131,11660–11661.
  • [11] Heravi M.M., Saeedi M., Beheshtiha Y.S., Oskooie H.A.,One-pot synthesis of benzochromeno-pyrazole derivatives,Mol. Divers., 2010, 15, 239-243; (b) Zhu J., Bienaymé H. (Eds);Wiley-VCH: Weinheim, 2005, ISBN 3-527-30806-7.
  • [12] (a) Starcevich J.T., Laughlin T.J., Mohan R.S., Iron(III) tosylatecatalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via the Biginelli reaction, Tetrahedron Lett., 2013,54, 983-985; (b) Harikrishnan P.S., Rajesh S. M., PerumalS., Almansour, A. I., Iron(III) tosylate catalyzed synthesis of3,4-dihydropyrimidin-2(1H)-ones/thiones via the Biginellireaction, Tetrahedron Lett., 2013, 54, 1076.[Crossref]
  • [13] Adib M., Ansari S., Feizi S., Bijanzadehb H.R., An EfficientThree-Component Synthesis of 3-(1-Hydroxyalkyl)[1,2,4]-triazolo[4,3-c]quinazolines, Synlett, 2010, 6, 921-923.
  • [14] Alagarsamy V., Solomonb, V.R., Dhanabal K., Synthesis andpharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic, anti-inflammatory agents,Bioorg. Med. Chem., 2007, 15, 235-241.[Crossref]
  • [15] Alagarsamya V., Pathak U.S., Synthesis and antihypertensiveactivity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones, Bioorg. Med. Chem., 2007, 15, 3457-3462.[Crossref]
  • [16] Liu J.F., Wilson C.J., Ye P., Sprague K., Sargent K., Si Y.,Beletsky G., Yohannes D., Ng, S.C., Privileged structure-basedquinazolinone natural product-templated libraries: Identificationof novel tubulin polymerization inhibitors, Bioorg.Med. Chem. Lett., 2006, 16, 686-690.[Crossref][PubMed]
  • [17] Francis R. D. EP Patent 315, 390, 1989.
  • [18] Itoh T., Mase T., A Novel Practical Synthesis of Benzothiazolesvia Pd-Catalyzed Thiol Cross-Coupling, Org. Lett., 2007, 9,3687-3689.[Crossref]
  • [19] Bondock S., Fadaly W., Metwally M.A., Enaminonitrile inheterocyclic synthesis: Synthesis and antimicrobial evaluationof some new pyrazole, isoxazole and pyrimidine derivativesincorporating a benzothiazole moiety, Eur. J. Med. Chem.,2009, 44, 4813–4818.[WoS][Crossref]
  • [20] Amnerkar N. D., Bhusari K. P., Anticonvulsant activity and3D-QSAR study of some prop-2-eneamido and 1-acetylpyrazolinderivatives of aminobenzothiazole, Eur. J. Med.Chem., 2010, 45,149–159.[Crossref]
  • [21] Havrylyuk D., Mosula L., Zimenkovsky B., Vasylenko O., GzellaA., Lesyk, R., Synthesis and anticancer activity evaluation of4-thiazolidinones containing benzothiazole moiety, Eur. J.Med. Chem., 2010, 45, 5012-5021.[Crossref]
  • [22] Saeed S., Rashid N., Jones P.G., Ali M., Hussain R., Synthesis,characterization and biological evaluation of some thioureaderivatives bearing benzothiazole moiety as potential antimicrobialand anticancer agents, Eur. J. Med. Chem., 2010, 45,1323-1331.[Crossref]
  • [23] Khalil A.M., Berghot M.A., Gouda M.A., Synthesis andantibacterial activity of some new thiazole and thiophenederivatives, Eur. J. Med. Chem., 2009, 44, 4434–4440.[Crossref]
  • [24] Wang Y., Klunk W.E., Debnath M.L., Huang G.F., Holt D.P., ShaoL., Mathis C.A., Development of a PET/SPECT agent for amyloidimaging in Alzheimer’s disease, J. Mol. Neurosci., 2004, 24(1),55-62.[Crossref]
  • [25] Yoshida M., Hayakawa I., Hayashi N., Agatsuma T., Oda Y.,Tanzawa F., Iwasaki S., Koyama K., Furukawa H., KurakataS., Synthesis and biological evaluation of benzothiazolederivatives as potent antitumor agents, Bioorg. Med. Chem.Lett., 2005, 15, 3328-3332.[Crossref]
  • [26] Solomon V.R., Hu C., Lee H., Hybrid pharmacophore designand synthesis of isatin–benzothiazole analogs for theiranti-breast cancer activity, Bioorg. Med. Chem., 2009, 17,7585-7592.[Crossref]
  • [27] Hossaini Z., Charati F.R., Soltani S., Mirzaei A., Berijani K.,Multicomponent reactions of ammonium thiocyanate, acylchlorides, alkyl bromides, and enaminones: A facile one-potsynthesis of thiophenes, Molecular Diversity, 2011, 15 (4),911-916.[WoS]
  • [28] Sperry J.B., Wright D.L., Furans, thiophenes and relatedheterocycles in drug discovery Current Opinion in DrugDiscovery and Development, Curr. Opin. Drug Discov. Devel.,2005, 8, 723-740.
  • [29] (a) Kumar M., Sharma K., Samarth R.M., Kumar A., Synthesisand antioxidant activity of quinolinobenzothiazinones, Eur.J. Med. Chem., 2010, 45, 4467-4472; (b) Gupta R.R., KumarM. “Synthesis, Reactions and Properties of Phenothiazines”in Phenothiazines and 1,4-Benzothiazines, Chemical andBiomedical Aspect. Elsevier: Amsterdam, 1998, 1-161.[Crossref]
  • [30] (a) Arya A.K., Kumar M., Base catalyzed multicomponentsynthesis of spiroheterocycles with fused heterosystems,Mol. Divers., 2011, 15, 781-789. (b) Arya A.K., Gupta, S.K.,Kumar M., A domino protocol for the efficient synthesis ofstructurally diverse benzothiazolylquinoline-2,5-diones andtheir spiro analogues, Tetrahedron Lett., 2012, 53, 6035-6038;(c) Kumar M., Sharma K., Arya A.K., Use of SO3H-functionalizedhalogenfree ionic liquid ([MIM(CH2)4SO3H] [HSO4]) as efficientpromoter for the synthesis of structurally diverse spiroheterocycles,Tetrahedron Lett., 2012, 53, 4604-4608; (d) KumarM., Sharma K., Sharma D.K., Arya A.K., An efficient, ionic liquidmediated one-pot, three component sequential synthesis of3-benzothiazolyl-2-styrylquinazolin-4(3H)-ones, Tetrahedronlett., 2013, 54, 878-882.
  • [31] Rathore B.S., Kumar M., Synthesis of7-chloro-5-trifluoromethyl/7-fluoro/7-trifluoromethyl-4H-1,4-benzothiazines as antimicrobial agents, Bioorg. Med.Chem., 2006, 14, 5678-5682.
  • [32] Rathore B.S., Gupta V., Gupta R.R., Kumar M., Synthesisof 7-chloro-5-trifluoromethyl/7-fluoro/7-trifluoromethyl-4H-1,4-phenothiazines, Heteroatom Chem., 2007, 18, 81-86;(b) Arya A.K., Kumar M., An efficient green chemical approachfor the synthesis of structurally diverse spiroheterocycles withfused heterosystem, Green Chem., 2011, 13, 1332–1338.
  • [33] (a) Sharma B.K., Sharma P.K., Kumar M., Diversity orientedone-pot three-component sequential synthesis of annulatedbenzothiazoloquinazolines, Synth. Commun., 2010, 40,2347-2352; (b) Rajawat A., Khandelwal S., Kumar M., Deepeutectic solvent promoted efficient and environmentallybenign four-component domino protocol for synthesis ofspirooxindoles, RSC Adv., 2014, 4, 5105-5112; (c) KhandelwalS., Rajawat A., Kumar M., An Efficient and environmentallybenign four-component domino protocol for synthesis ofspirooxindoles spiroannulated with fused heterosystems ofprivileged heterocycles, Current Bioactive Compounds, 2013, 9,203-210.
  • [34] (a) Nagarapu L., Gaikwad H.K., Palem J.D., Venkatesh R., BantuR., Sridhar B., Convenient approach for the one- pot, threecomponentsynthesis of triheterocyclic 4H-pyrimido[2,1-b]benzothiazole derivatives using TBAHS, Synth. Comm., 2013,43, 93–104; (b) Pavlenko A., Shikhaliev K.S., Potapov A.Y.,Krylsky D.V., Three-component reaction of 2-aminobenzothiazolewith methylene-active carbonyl compounds andaldehydes, Chemistry of Heterocyclic Compounds, 2005,41, 689-690; (c) Kidwai M., Chauhan R., Bhatnagar D.,Amberlyst-15® in PEG: A novel catalytic system for the facileand efficient one-pot synthesis of benzothiazolo-[2,3-b]-quinazolinone derivatives, Science china chemistry, 2012, 55,2154-2160;
  • [35] (a) Arya D., Tomar, R., Rawat D. S., Greener synthesisand photo-antiproliferative activity of novel fluorinatedbenzothiazolo[2, 3-b]quinazolines, Med. Chem. Res., 2014,23, 896–904; (b) Shah N. K., Patel M. P., Patel, R. G. One-pot,multicomponent condensation reaction in neutral conditions:synthesis, characterization, and biological studies of fusedthiazolo[2,3-b]quinazolinone derivatives, Phosphorus, Sulfur,and Silicon, 2009, 184, 2704–2719, 2009.

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