Abstract
An efficient method for the synthesis of S-aryl /heteroaryl-quinazoline has been developed through the cross-coupling of 1,4-dihydroquinazoline with a variety of aryl and heteroaryl boronic acids assisted by [Cu(OAc) 2] as the catalyst for the formation of carbon-sulfur bonds. This newly developed method demonstrates that the conditions of the traditional copper-catalyzed Chan-Lam reaction can be improved. Optimized reaction involves base, solvent and catalyst.
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(a) Herz W, Grisebach H, Kirby G W and Tamm C 1984 In Progress in the Chemistry of Organic Natural Products S Johne (Ed.) (Wien: Spinger–Verlag) 46 p.159; (b) Brossi A 1986 The Alkaloids, Chemistry and Pharmacology S Johne (Ed.) (New York: Academic Press) 29 p. 99
(a) Yudin A K and Hartwig J F 2010 Catalyzed Carbon-Heteroatom Bond Formation (Weinheim: Wiley VCH); (b) Hartwig J F 1998 Carbon-Heteroatom Bond-Forming Reductive Eliminations of Amines, Ethers, and Sulfides Acc. Chem. Res. 31 852; (c) Hartwig J F 1998 Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: Scope and Mechanism Angew. Chem. Int. Ed. 37 2046; (d) Ley S V and Thomas A W 2003 Modern synthetic methods for copper mediated C(aryl)[bond]O, C(aryl)[bond]N, and C(aryl)[bond]S bond formation Angew. Chem. Int. Ed. 42 5400; (e) Beccalli E M, Broggini G, Martinelli M and Sottocornola S 2007 C-C, C-O, C-N bond formation on SP2 Carbon by Pd (II)-catalyzed reactions involving oxidant agents Chem. Rev. 107 5318; (f) Monnier F and Taillefer M M 2009 Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions Angew. Chem. Int. Ed. 48 6954
(a) Bernardi F, Csizmadia I G and Mangini A 1985 In Organic Sulfur Chemistry: Theoretical and Experimental Advances (Amsterdam: Elsevier) 19; (b) De Martino G, Edler M C, La Regina G, Coluccia A, Barbera M C, Barrow D, Nicholson R I, Chiosis G, Brancale A, Hamel E, Artico M and Silvestri R 2006 New arylthioindoles: Potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies J. Med. Chem. 49 947; (c) Gangjee A, Zeng Y, Talreja T, McGuire J J, Kisliuk R L and Queener S F 2007 Design and synthesis of classical and non-classical 6-arylthio-2,4-diamino-5-ethylpyrrolo[2,3-d]pyrimidines as antifolates J. Med. Chem. 50 3046
(a) Tiecco M 1988 Selective Dealkylations of Aryl Alkyl Ethers, Thioethers and Selenoethers Synthesis 10 749; (b) Thuillier A and Metzner P 1994 Sulfur Reagents in Organic Synthesis: Tellurium-containing Heterocycles (New York: Academic Press)
(a) Kondo T and Mitsudo T 2000 Metal catalyzed carbon-sulfur bond formation Chem. Rev. 100 3205; (b) Correa A, Carril M and Bolm C 2008 Iron catalyzed S-arylation of thiols with aryl iodides Angew. Chem. Int. Ed. 47 2880; (c) Gangjee A, Zeng Y, Talreja T, McGuire J J, Kisliuk R L and Queener S F 2007 Design and synthesis of classical and non classical 6-arylthio-2,4-diamino-5-ethyl pyrrolo[2,3-d]pyrimidines as antifolates J. Med. Chem. 50 3046
(a) Tietze L F 1996 Domino Reactions in organic synthesis Chem. Rev. 96 115; (b) Tietze L F and Rackelmann N 2004 Domino reactions in the synthesis of heterocyclic natural products and analogs Pure Appl. Chem. 76 1967; (c) Wasilke J C, Obrey S J, Baker R T and Bazan G C 2005 Concurrent tandem catalysis Chem. Rev. 105 1001; (d) Sunderhaus J D and Martin S F 2009 Applications of Multicomponent Reactions to the Synthesis of Diverse Heterocyclic Scaffolds Chem. Eur. J. 15 1300
Hua-Jian X, Yong-Qiang Z, Teng F and Yi-Si F 2012 Chan–Lam-Type S-Arylation of Thiols with Boronic Acids at Room Temperature J. Org. Chem. 77 2878
(a) Chan D M T, Monaco K L, Wang R P and Winters M P 1998 New N- and O-arylations with phenyl boronic acids and cupric acetate Tetrahedron Lett. 39 2933; (b) Lam P Y S, Clark C G, Saubern S, Adams J, Winters M P, Chan D M T and Combs A 1998 New aryl/heteroaryl C-N bond cross coupling reactions via arylboronicacid/cupric acetae arylation Tetrahedron Lett. 39 2941
Cundy D J and Forsyth S A 1998 Cupric Acetate Mediated N-Arylation by Arylboronic Acids: A Preliminary Investigation into the Scope of Application Tetrahedron Lett. 39 7979
Evans D A, Katz J L and West T R 1998 Synthesis of Diaryl ethers through the copper promoted Arylation of phenols with Aryl boronicacids: An Expedient synthesis of Thyroxine Tetrahedron Lett. 39 2937
Satya K P, Ramana M R V V, Reddy M R P, Naresh K K and Srinivas K 2016 Tandem one pot (Top) and efficient method for the palladium reagent-catalyzed cross coupling of quinazoline thiols J. Het. Chem. 53 784
Parthasarathi D, Kiran Kumar C, Naresh K K, Md I., Javed I and Srinivas N 2008 Dithiocarbamate and CUO promoted one-pot synthesis of 2-(N-substituted)-aminobenzimidazoles and related heterocycles Tetrahedron Lett. 49 992
Naresh K K, Sreeramamurthy K, Sadananda P, Mukkanti K and Parthasarathi D 2010 Dithiocarbamate and DBU promoted amide bond formation under microwave condition Tetrahedron Lett. 51 899
Naresh K K, Venkatanarayana M and Srinivas K 2015 Dithiocarbamate promoted practical Synthesis of N-Aryl-2-aminobenzazoles: Synthesis of novel Aurora-A kinase inhibitor J. Chem. Sci. 127 447
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Pulakhandam S K is thankful to the authorities of Jawaharlal Nehru Technological University Kakinada for registration and GITAM University Hyderabad for providing laboratory facilities.
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NMR, IR and mass spectra of the synthesized compounds are reported in Supplementary Information, available at www.ias.ac.in/chemsci.
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PULAKHANDAM, S.K., KATARI, N.K. & MANDA, R.P.R. Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S Bond formation by “Chan-Lam Cross-Coupling” Reaction. J Chem Sci 129, 203–210 (2017). https://doi.org/10.1007/s12039-016-1217-7
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DOI: https://doi.org/10.1007/s12039-016-1217-7