Ionic liquid-supported synthesis of dihydroquinazolines and tetrahydroquinazolines under microwave irradiation

Schreiber SL (2005) Small molecules: the missing link in the central dogma. Nat Chem Biol 1: 64–66. doi:10.1038/nchembio0705-64 Collins I, Workman P (2006) New approaches to molecular cancer therapeutics. Nat Chem Biol 2: 689–700. doi:10.1038/nchembio840 Connolly DJ, Cusack D, Sullivan TPO, Guiry PJ (2005) Synthesis of quinazolinones and quinazolines. Tetrahedron 61: 10153–10202. doi:10.1016/j.tet.2005.07.010 Baxter EW, Conway KA, Kennis L, Bischoff F, Mercken MH, De Winter HL, Reynolds CH, Tounge BA, Luo C, Scott MK, Huang Y, Braeken M, Pieters SMA, Berthelot DJC, Masure S, Bruinzeel WD, Jordan AD, Parker MH, Boyd RE, Qu J, Alexander RS, Brenneman DE, Reitz AB (2007) 2-Amino-3,4-dihydroquinazolines as inhibitors of bace-1 (β-site app cleaving enzyme): use of structure based design to convert a micromolar hit into a nanomolar lead. J Med Chem 50: 4261–4264. doi:10.1021/jm0705408 Marzaro G, Guiotto A, Pastorini G, Chilin A (2010) A novel approach to quinazolin-4(3H)-one via quinazoline oxidation: an improved synthesis of 4-anilinoquinazolines. Tetrahedron 66: 962–968. doi:10.1016/j.tet.2009.11.091 Hennequin LF, Allen J, Breed J, Curwen J, Fennell M, Green TP, Brempt CLV, Morgentin R, Norman RA, Olivier A, Otterbein L, Ple PA, Warin N, Costello G (2006) N-(5-Chloro-1,3-benzodioxol-4-yl)-7-[2-(4-methylpiperazin-1-yl)ethoxy]-5-(tetrahyd-ro-2H-pyran-4-yloxy)-quinazolin-4-amine, a novel, highly selective, orally available, dual-specific c-Src/Abl kinase inhibitor. J Med Chem 49: 6465–6488. doi:10.1021/jm060434q Zuccotto F, Ardini E, Casale E, Angiolini M (2010) Through the “gatekeeper door”: exploiting the active kinase conformation. J Med Chem 45: 2681–2694. doi:10.1021/jm901443h Cai X, Zhai HX, Wang J, Forrester J, Qu H, Yin L, Lai CJ, Bao R, Qian C (2010) Discovery of 7-(4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-yloxy)-N-hydroxyheptanamide (CUDC-101) as a potent multi-acting HDAC, EGFR, and HER2 inhibitor for the treatment of cancer. J Med Chem 53: 2000–2009. doi:10.1021/jm901453q Lee YS, Lee BH, Park SJ, Kang SB, Rhim H, Park JY, Lee JH, S.W. J, Lee JY (2004) 3,4-Dihydroquinazoline derivatives as novel selective T-type Ca2+ channel blockers. Bioorg Med Chem Lett 14: 3379–3384. doi:10.1016/j.bmcl.2004.04.090 Rhim H, Lee YS, Park SJ, Y. CB, Lee JY (2005) Synthesis and biological activity of 3,4-dihydroquinazolines for selective T-type Ca2+ channel blockers. Bioorg Med Chem Lett 15: 283–286. doi:10.1016/j.bmcl.2004.10.078 Park SJ, Park SJ, Lee MJ, Rhim H, Kim Y, Lee J-H, Chung BY, Lee JY (2006) Synthesis and SAR studies of a novel series of T-type calcium channel blockers. Bioorg Med Chem 14: 3502–3511. doi:10.1016/j.bmc.2006.01.005 Choi JY, Seo HN, Lee MJ, Park SJ, Park SJ, Jeon JY, Kang JH, Pae AN, Rhim H, Lee JY (2007) Synthesis and biological evaluation of novel T-type calcium channel blockers. Bioorg Med Chem Lett 17: 471–475. doi:10.1016/j.bmcl.2006.10.024 Michael JP (2008) Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep 25: 166–187. doi:10.1039/B612168N Pao W, Miller VA, Kris MG (2004) Targeting the epidermal growth factor receptor tyrosine kinase with gefitinib (Iressa®) in non-small cell lung cancer (NSCLC). Semin Cancer Biol 14: 33–40. doi:10.1016/j.semcancer.2003.11.005 Garofalo A, Goossens L, Baldeyrou B, Lemoine Al, Ravez Sv, Six P, David-Cordonnier M-H, Bonte J-P, Depreux P, Lansiaux Al, Goossens JF (2010) Design, synthesis, and DNA-binding of N-alkyl(anilino)quinazoline derivatives. J Med Chem 53: 8089–8103. doi:10.1021/jm1009605 Merrifield RB (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Soc Chem 85: 2149–2154. doi:10.1021/ja00897a025 Booth RJ, Hodges JC (1999) Solid-supported reagent strategies for rapid purification of combinatorial synthesis products. Acc Chem Res 32: 18–26. doi:10.1021/ar970311n Gravert DJ, Janda KD (1997) Organic synthesis on soluble polymer supports: liquid-phase methodologies. Chem Rev 97: 489–510. doi:10.1021/cr960064l Toy PH, Janda KD (2000) Soluble polymer-supported organic synthesis. Acc Chem Res 33: 546–554. doi:10.1021/ar990140h Lu J, Toy PH (2009) Organic polymer supports for synthesis and for reagent and catalyst immobilization. Chem Rev 109: 815–838. doi:10.1021/cr8004444 Miura T, Hirose Y, Ohmae M, Inazu T (2001) Fluorous oligosaccharide synthesis using a novel fluorous protective group. Org Lett 3: 3947–3950. doi:10.1021/ol016838o Miura T, Goto K, Waragai H, Matsumoto H, Hirose Y, Ohmae M, Ishida H, Satoh A, Inazu T (2004) Rapid oligosaccharide synthesis using a fluorous protective group. J Org Chem 69: 5348–5353. doi:10.1021/jo049425k Zhang W, Lu Y, Chen CHT, Zeng L, Kassel DB (2006) Fluorous mixture synthesis of two libraries with hydantoin- and benzodiazepinedione-fused heterocyclic scaffolds. J Comb Chem 8: 687–695. doi:10.1021/cc060061e Zhang W (2009) Fluorous linker-facilitated chemical synthesis. Chem Rev 109: 749–795. doi:10.1021/cr800412s Earle MJ, Seddon KR (2000) Ionic liquids. Green solvents for the future. Pure Appl Chem 72: 1391–1398. doi:10.1351/pac200072071391 Trost BM (1995) Atom economy—a challenge for organic synthesis: homogeneous catalysis leads the way. Angew Chem Int Ed 34: 259–281. doi:10.1002/anie.199502591 Miao W, Chan TH (2003) Exploration of ionic liquids as soluble supports for organic synthesis, demonstration with a Suzuki coupling reaction. Org Lett 5: 5003–5005. doi:10.1021/ol035977y Miao W, Chan TH (2006) Ionic-liquid-supported synthesis: a novel liquid-phase strategy for organic synthesis. Acc Chem Res 39: 897–908. doi:10.1021/ar030252f Donga RA, Khaliq-Uz-Zaman SM, Chan T-H, Damha MJ (2006) A novel approach to oligonucleotide synthesis using an imidazolium ion tag as a soluble support. J Org Chem 71: 7907–7910. doi:10.1021/jo061279q Legeay JC, Goujon JY, Eynde JJV, Toupet L, Bazureau JP (2006) Liquid-phase synthesis of polyhydroquinoline using task-specific ionic liquid technology. J Comb Chem 8: 829–833. doi:10.1021/cc0600425 Pathak AK, Yerneni CK, Young Z, Pathak V (2008) Oligomannan synthesis using ionic liquid supported glycosylation. Org Lett 10: 145–148. doi:10.1021/ol702743x Martins MAP, Frizzo CP, Moreira DN, Zanatta N, Bonacorso HG (2008) Ionic liquids in heterocyclic synthesis. Chem Rev 108: 2015–2050. doi:10.1021/cr078399y Loupy A (2006) Microwaves in organic synthesis, 2nd edn. Wiley, Weinheim Dallinger D, Kappe CO (2007) Microwave-assisted synthesis in water as solvent. Chem Rev 107: 2563–2591. doi:10.1021/cr0509410 Maiti B, Chanda K, Sun CM (2009) Traceless synthesis of hydantoin fused tetrahydro-β-carboline on ionic liquid support in green media. Org Lett 11: 4826–4829. doi:10.1021/ol901857h Yellol GS, Tsai WC, Sun CM (2010) Novel cyclization of bis-Boc-guanidines: expeditive traceless synthesis of 1,3,5-oxadiazinones under microwave conditions. Chem Commun 46: 9170–9172. doi:10.1039/C0CC03519J Hsiao YS, Yellol GS, Chen LH, Sun CM (2010) Multidisciplinary synthetic approach for rapid combinatorial library synthesis of triaza-fluorenes. J Comb Chem 12: 723–732. doi:10.1021/cc1000902 Chanda K, Maiti B, Yellol G, Chien MH, Kuo ML, M. SC (2011) Polymer supported synthesis of novel benzoxazole linked benzimidazoles under microwave conditions: In vitro evaluation of VEGFR-3 kinase inhibition activity. Org Biomol Chem 9: 1917–1926. doi:10.1039/C0OB00547A Glasnov TN, Stadlbauer W, Kappe C (2005) Microwave-assisted multistep synthesis of functionalized 4-arylquinolin-2(1h)-ones using palladium-catalyzed cross-coupling chemistry. J Org Chem 70: 3864–3870. doi:10.1021/jo0502549 Ye P, Sargent K, Stewart E, Liu JF, Yohannes D, Yu L (2006) Novel and expeditious microwave-assisted three-component reactions for the synthesis of spiroimidazolin-4-ones. J Org Chem 71: 3137–3140. doi:10.1021/jo060228q Crestey F, Witt M, Frydenvang K, Stærk D, Jaroszewski JW, Franzyk H (2008) Microwave-assisted ring-opening of activated aziridines with resin-bound amines. J Org Chem 73: 3566–3569. doi:10.1021/jo702612u Holt JJ, Calitree BD, Vincek J, Gannon MK, Detty MR (2007) A Microwave-assisted synthesis of julolidine-9-carboxamide derivatives and their conversion to chalcogenoxanthones via directed metalation. J Org Chem 72: 2690–2693. doi:10.1021/jo070086f Horikoshi S, Iida S, Kajitani M, Sato S, Serpone N (2008) Chemical reactions with a novel 5.8-GHz microwave apparatus. 1. characterization of properties of common solvents and application in a Diels-Alder organic synthesis. Org Process Res Dev 12: 257–263. doi:10.1021/op700292s Bendale PM, Sun CM (2002) Rapid microwave-assisted liquid-phase combinatorial synthesis of 2-(arylamino)benzimidazoles. J Comb Chem 4: 359–361. doi:10.1021/cc0200080 Yeh WB, Sun CM (2004) Soluble polymer-supported synthesis of thioxotetrapyrimidinone by focused microwave irradiation. J Comb Chem 6: 279–282. doi:10.1021/cc034070o Chen CH, Chien MH, Kuo ML, Chou CT, Lai JJ, Lin SF, Thummanagoti S, Sun CM (2009) Diversity-oriented synthesis of angular bis-benzimidazole derivatives under microwave irradiation. J Comb Chem 11: 1038–1046. doi:10.1021/cc900084s Chanda K, Kuo J, Chen CH, Sun CM (2009) Enantioselective synthesis of benzimidazolyl quinoxalinones on soluble polymer support using focused microwave irradiation. J Comb Chem 11: 252–260. doi:10.1021/cc800137p