Solid-phase synthesis of sulfur containing heterocycles

References

• Elleby B, Chirica LCC, Tu ZM, et al. Characterisation of carbonic anhydrase from Neisseria gonorrhoeae. Eur J Biochem. 2001;268:1613–1619.
   PubMedGoogle Scholar
• Kaur N. Microwave-assisted synthesis of five membered S-heterocycles. J Iranian Chem Soc. 2014;11:523-564.
   Web of Science ®Google Scholar
• Koradin C, Dohle W, Rodriguez AL, et al. Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases. Tetrahedron. 2003;59:1571–1587.
   Web of Science ®Google Scholar
• Badami BV. Mesoionic compounds. Resonance. 2006;11:40–48.
   Google Scholar
• Kamble RR, Sudha BS. Synthesis and pharmacological evaluation of 1,5-benzothiazepine derivatives. Phosphorus Sulfur Silicon Relat Elem. 2008;183:1691–1709.
   Web of Science ®Google Scholar
• Kaur N. Palladium-catalyzed approach to the synthesis of S-heterocycles. Catal Rev. 2015;57:478–564.
   Web of Science ®Google Scholar
• Jumat S, Nadia S, Emad Y, et al. Synthesis, characterization and biological activity of Schiff bases of 2,5-dimercapto-1,3,4-thiadiazole. Aus J Basic App Sci. 2010;4:2016–2021.
   Google Scholar
• Kaur N, Kishore D. Nitrogen-containing six-membered heterocycles: solid-phase synthesis. Synth Commun. 2014;44:1173–1211.
   Web of Science ®Google Scholar
• Kaur N, Kishore D. Solid-phase synthetic approach toward the synthesis of oxygen containing heterocycles. Synth Commun. 2014;44:1019–1042.
   Web of Science ®Google Scholar
• Dwivedi J, Kaur N, Kishore D, et al. Synthetic and biological aspects of thiadiazoles and their condensed derivatives: an overview. Curr Top Med Chem. 2016;16:2884–2920.
   PubMed Web of Science ®Google Scholar
• Amarish BS, Nandini RP. Synthesis of novel aryloxy propanoyl thiadiazoles as potential antihypertensive agents. J Chinese Chem Soc. 2010;57:1327–1330.
   Web of Science ®Google Scholar
• Bouillon I, Krchňák V. Efficient solid-phase synthesis of 3-substituted-5-oxo-5H-thiazolo[2,3-b]-quinazoline-8-carboxamides under mild conditions with two diversity positions. J Comb Chem. 2007;9:912–915.
   PubMedGoogle Scholar
• Pant UC, Chandra H, Goyal S. Synthesis and antimicrobial studies of 10-subtituted-6,7-dihydro-6H-7-(4-flourophenyl)-6-phenyl[1]benzopyrano[3,4-c][1,5]benzo thiazepines. Ind J Chem. 2006;45B:752.
   Google Scholar
• Cherkupally SR, Gurrala PR, Adki N, et al. Synthesis and biological study of novel methylene-bis-benzofuranyl-1,5-benzothiazepines. Org Commun. 2008;4:84–94.
   Google Scholar
• Kaur N. Microwave-assisted synthesis of seven membered S-heterocycles. Synth Commun. 2014;44:3201-3228.
   Web of Science ®Google Scholar
• Christensen C, Schiodt CB, Foged NT, et al. Solid phase combinatorial library of 1,3-azole containing peptides for the discovery of matrix metallo proteinase inhibitors. QSAR Comb Sci. 2003;22:754–766.
   Google Scholar
• Kaur N, Kishore D. Microwave-assisted synthesis of six-membered S-heterocycles. Synth Commun. 2014;44:2615–2644.
   Web of Science ®Google Scholar
• Kaur N, Dwivedi J, Kishore D. Solid-phase synthesis of nitrogen containing five-membered heterocycles. Synth Commun. 2014;44:1671–1729.
   Web of Science ®Google Scholar
• Kaur N. Solid-phase synthetic approach to the synthesis of azepine heterocycles of medicinal interest. Int J Pharma Bio Sci. 2013;4:357–372.
   Google Scholar
• Yamazaki S. Three or four heteroatoms including at least one selenium or tellurium, Reference Module in Chemistry, Molecular Sciences and Chemical Engineering Comprehensive Heterocyclic Chemistry III 2008, Vol. 6, Other five-membered rings with three or more heteroatoms, and their fused carbocyclic derivatives, 517–581.
   Google Scholar
• Kreis M, Nising CF, Schroen M, et al. Efficient solid phase synthesis of benzo[1,2,3]thiadiazoles and related structures. Org Biomol Chem. 2005;3:1835–1837.
   PubMed Web of Science ®Google Scholar
• Wang Y, Wilson SR. Solid phase synthesis of 2,3-dihydro-4-pyridones: reaction of Danishefsky’s diene with polymer-bound imines. Tetrahedron Lett. 1997;38:4021–4024.
   Web of Science ®Google Scholar
• Dahan A, Portnoy M. Synthesis of poly(aryl benzyl ether) dendrimers on solid support. Macromolecules. 2003;36:1034–1038.
   Web of Science ®Google Scholar
• Rink H. Solid-phase synthesis of protected peptide fragments using a trialkoxy-diphenyl-methylester resin. Tetrahedron Lett. 1987;28:3787–3790.
   Web of Science ®Google Scholar
• Mellor SL, Chan WC. 4-[2,4-Dimethoxyphenyl(N-fluoren-9-ylmethoxycarbonyl-N-alkylaminooxy)-methyl]phenoxymethyl polystyrene: a multiple solid-phase approach to N-alkylhydroxamic acids. J Chem Soc Chem Commun. 1997; 38:2005–2006.
   Google Scholar
• Vaino AR, Janda KD. Solid-phase organic synthesis: a critical understanding of the resin. JComb Chem. 2000;2:579–596.
   PubMed Web of Science ®Google Scholar
• Zaragoza F. Solid-phase synthesis of substituted 3-aminothiophenes and 2-methylene-2,3-dihydrothiazoles. Tetrahedron Lett. 1996;37:6213–6216.
   Web of Science ®Google Scholar
• Redemann T, Brooks ME, Jung G. Solid-Phase Synth. Comb. Libr., Collect. Pap., 5th Int. Symp. Epton, R., Ed.; Mayflower Scientific Ltd.: Kingswinford, U.K.; 1999. p. 377–380.
   Google Scholar
• Stephensen H, Zaragoza F. Resin-bound isothiocyanates as intermediates for the solid-phase synthesis of substituted thiophenes, Solid-Phase Organic Syntheses; Czarnik, A. W., Ed.; Wiley: New York, 2001;1:149–157.
   Google Scholar
• Whitehouse DL, Savinov SN, Austin DJ. An improved synthesis and selective coupling of a hydroxy based photolabile linker for solid phase organic synthesis. Tetrahedron Lett. 1997;38:7851–7852.
   Web of Science ®Google Scholar
• Castanedo GM, Sutherlin DP. Synthesis of tetrasubstituted thiophenes on solid-support using the Gewald reaction. Tetrahedron Lett. 2001;42:7181–7184.
   Web of Science ®Google Scholar
• Zhang MH, Wang HX, Zhao JX, et al. A rapid solid-phase synthesis to soluble oligothiophene molecular wires. Chinese Chem Lett. 2006;17:437–440.
   Web of Science ®Google Scholar
• Turner JD, Anemian R, Mackie RP, et al. Towards a general solid phase approach for the iterative synthesis of conjugated oligomers using a germanium based linker-first solid phase synthesis of an oligo-(triarylamine). Org Biomol Chem. 2007;5:1752–1763.
   PubMed Web of Science ®Google Scholar
• Puterova Z, Krutosikova A, Veghc D. Gewald reaction: Synthesis, properties and applications of substituted 2-aminothiophenes. ARKIVOC. 2010;(i):209–246.
   Google Scholar
• Hartley RC, McKiernan GJ. Titanium reagents for the alkylidenation of carboxylic acid and carbonic acid derivatives. J Chem Soc Perkin Trans. 1. 2002: 2763–2793.
   Google Scholar
• Roberts FC, Hartley CR. Titanium reagents for the synthesis of 2-substituted benzo[b]thiophenes on the solid phase. J Org Chem. 2004;69:6145–6148.
   PubMed Web of Science ®Google Scholar
• Bui TC, Flynn LB. Solid-phase synthesis of 2,3-disubstituted benzo[b]thiophenes and benzo[b]selenophenes. J Comb Chem. 2006;8:163–167.
   PubMed Web of Science ®Google Scholar
• Patro B, Merrett M, Murphy JA, et al. Radical-polar crossover reactions with polymer-supported tetrathiafulvalene. Tetrahedron Lett. 1999;40:7857–7860.
   Web of Science ®Google Scholar
• Mirizzi D, Pulici M. From polymer to small organic molecules: a tight relationship between radical chemistry and solid-phase organic synthesis. Molecules. 2011;16:3252–3314.
   PubMed Web of Science ®Google Scholar
• Yoo DJ, Greenberg MM. Synthesis of oligonucleotides containing 3'-alkyl carboxylic-acids using universal, photolabile solid-phase synthesis supports. J Org Chem. 1995;60:3358–3364.
   Web of Science ®Google Scholar
• Patek M, Drake B, Lebl M. Solid-phase synthesis of small organic molecules based on thiazolidine scaffold. Tetrahedron Lett. 1995;36:2227–2230.
   Web of Science ®Google Scholar
• Holmes CP, Jones DG. Reagents for combinatorial organic synthesis: development of a new o-nitrobenzyl photolabile linker for solid-phase synthesis. J Org Chem. 1995;60:2318–2319.
   Web of Science ®Google Scholar
• Holmes CP, Chinn JP, Look GC, et al. Strategies for combinatorial organic synthesis: solution and polymer-supported synthesis of 4-thiazolidinones and 4-metathiazanones derived from amino acids. J Org Chem. 1995;60:7328–7333.
   Web of Science ®Google Scholar
• Pons JF, Mishir Q, Nouvet A, et al. Thiazole formation via traceless cleavage of Rink resin. Tetrahedron Lett. 2000;41:4965–4968.
   Web of Science ®Google Scholar
• Mohler DL, Shena G, Dotse AK. Solution and solid-phase synthesis of peptide-substituted thiazolidinediones as potential PPAR ligands. Bioorg Med Chem Lett. 2000;10:2239–2242.
   PubMed Web of Science ®Google Scholar
• Attanasi OA, De Crescentini L, Filippone P, et al. Solid-phase synthesis of 4-triphenylphosphoranylidene-4,5-dihydropyrazole-5-ones, 4-aminocarbonyl-pyrazoles, 4-methoxy-1H-pyrazole-5(2H)-ones and 2-thiazolidin-4-ones from polymer-bound 1,2-diaza-1,3-butadienes. Tetrahedron. 2001;57:5855–5863.
   Web of Science ®Google Scholar
• Králová P, Fülöpová V, Maloň M, et al. Stereoselective polymer-supported synthesis of morpholine- and thiomorpholine-3-carboxylic acid derivatives. ACS Comb Sci. 2017;19:173–180.
   PubMed Web of Science ®Google Scholar
• You SL, Kelly JW. Total synthesis of didmolamides A and B. Tetrahedron Lett. 2005;46:2567–2570.
   Web of Science ®Google Scholar
• Gomez L, Gellibert F, Wagner A, et al. Solid-phase synthesis of tetrasubstituted 2-imino-1,3-thiazolines using a functionalizing cleavage strategy. Tetrahedron Lett. 2008;49:2726–2729.
   Web of Science ®Google Scholar
• Katritzky AR, Cai X, Rogovoy BV. Solid-phase synthesis and application of trisubstituted thioureas. J Comb Chem. 2002;5:392–399.
   Google Scholar
• Said EK, Sabine B, Abderrahim M, et al. Solid support synthesis of 2,4-disubstituted thiazoles and aminothiazoles. Tetrahedron Lett. 2002;43:3193–3196.
   Web of Science ®Google Scholar
• Kim KS, Kimball SD, Misra NR, et al. Discovery of aminothiazole inhibitors of cyclin-dependent kinase 2: synthesis, X-ray crystallographic analysis, and biological activities. J Med Chem. 2002;45:3905–3927.
   PubMed Web of Science ®Google Scholar
• Johnson SG, Connolly PJ, Murray WV. A concise synthesis of 7-chloro-2-methylsulfanyl-thiazolo[4,5-b]pyridine-6-carbonitrile, a versatile intermediate for substituted 6-cyanothiazolopyridines. Tetrahedron Lett. 2006;47:4853–4856.
   Web of Science ®Google Scholar
• Biron E, Chatterjee J, Kessler H. Solid-phase synthesis of 1,3-azole-based peptides and peptidomimetics. Org Lett. 2006;8:2417–2420.
   PubMed Web of Science ®Google Scholar
• Nefzi A, Arutyunyan S, Fenwick EJ. Two-steps Hantzsch based macrocyclization approach for the synthesis of thiazole containing cyclopeptides. J Org Chem. 2010;75:7939–7941.
   Web of Science ®Google Scholar
• South SM, Dice AT, Girard JT, et al. Polymer-assisted solution-phase (PASP) parallel synthesis of an ketothiazole library as tissue factor VIIa inhibitors. Bioorg Med Chem Lett. 2003;13:2363–2367.
   PubMed Web of Science ®Google Scholar
• Králová P, Maloň M, Volná T, et al. Polymer-supported stereoselective synthesis of benzoxazino[4,3-b][1,2,5]thiadiazepinone 6,6-dioxides. ACS Comb Sci. 2017;19:670–674.
   PubMed Web of Science ®Google Scholar
• Lee CL, Lam Y, Lee SY. Solid-phase combinatorial synthesis of benzothiazole and 2,3-dihydro-[1,5]-benzothiazepine derivatives. Tetrahedron Lett. 2001;42:109–111.
   Web of Science ®Google Scholar
• Soural M, Bouillon I, Krchňák V. Combinatorial libraries of bis-heterocyclic compounds with skeletal diversity. J Comb Chem. 2008;10:923–933.
   PubMedGoogle Scholar
• Huanga X, Tang J. Solid phase synthesis of benzothiazole and thiophene derivatives based on resin-bound cyclic malonic acid ester. Tetrahedron. 2003;59:4851–4856.
   Google Scholar
• Thomae D, Perspicace E, Hesse S, et al. Synthesis of substituted [1,3]thiazolo[4,5-b]pyridines and [1,3]thiazolo[4,5-d][1,2,3]triazines. Tetrahedron. 2008;64:9309–9314.
   Web of Science ®Google Scholar
• Lee T, Park JH, Lee DH, et al. Traceless solid-phase synthesis of 2,4,6-trisubstituted thiazolo[4,5-d]pyrimidine-5,7-dione derivatives. J Comb Chem. 2009;11:495–499.
   PubMed Web of Science ®Google Scholar
• Kaur, N. Greener and expeditious synthesis of fused six-membered N,N-heterocycles using microwave irradiation. Synth Commun. 2015;45:1493–1519.
   Web of Science ®Google Scholar
• Albericio F, Garcia J, Michelotti LE, et al. Solid phase synthesis of sulfahydantoins. Tetrahedron Lett. 2000;41:3161–3163.
   Web of Science ®Google Scholar
• Kilburn JP, Laua J, Jones RCF. Solid-phase synthesis of substituted 1,3,4-thiadiazoles. Tetrahedron Lett. 2003;44:7825–7828.
   Web of Science ®Google Scholar
• Kappel CJ, Yokum TS, Barany G. Parallel solid-phase syntheses of 1,3,4-thiadiazolium-2-aminides. J Comb Chem. 2004;6:746–752.
   PubMed Web of Science ®Google Scholar
• Gong Y, Lee T. Combinatorial syntheses of five-membered ring heterocycles using carbon disulfide and a solid support. J Comb Chem. 2010;12:393–409.
   PubMed Web of Science ®Google Scholar
• Liu Z, Song Z, Zhao J, et al. Solid-phase synthesis of 2-arylamino-5-(4-hydroxyphenyl)-1,3,4-thiadiazole derivatives based on resin-bound acylhydrazines. Phosphorus Sulfur Silicon. 2010;185:2375–2381.
   Web of Science ®Google Scholar
• Mortezaei R, Ida S, Campbell DA. Preparation of N-alkylated 5-oxo-3-carboxamyl-1,4-thiazinanes on solid support. Mol Divers. 1998;4:143–148.
   PubMed Web of Science ®Google Scholar
• Saruta K, Ogiku T. A traceless solid phase synthesis of thiomorpholin-3-ones. Tetrahedron Lett. 2008;49:424–427.
   Web of Science ®Google Scholar
• Schwarz MK, Tumelty D, Gallop MA. Solid-phase synthesis of 3,5-disubstituted 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones. J Org Chem. 1999;64:2219–2231.
   Web of Science ®Google Scholar
• Menichetti S, Mori M, Nativi C. Hetero Diels–Alder reactions (HDAR) of α,α′-dioxothiones on solid support. Tetrahedron. 2005;61:5005–5010.
   Web of Science ®Google Scholar
• Feliu L, Vera-Luque P, Albericio F, et al. Advances in solid-phase cycloadditions for heterocyclic synthesis. J Comb Chem. 2007;9:521–565.
   PubMedGoogle Scholar
• Burgess K. Solid-phase organic synthesis. New York: John Wiley & Sons; 2000.
   Google Scholar
• Bittner S, Assaf Y, Krief P, et al. Synthesis of N-acyl-, N-sulfonyl-, and N-phosphinylphospha(PV)azenes by a redox-condensation reaction using amides, triphenylphosphine, and diethyl azodicarboxylate. J Org Chem. 1985;50:1712–1718.
   Web of Science ®Google Scholar
• McMaster C, Fülöpová V, Popa I, et al. Solid-phase synthesis of anagrelide sulfonyl analogues. ACS Comb Sci. 2014;16:221–224.
   PubMed Web of Science ®Google Scholar
• Cankařová N, Venia AL, Krchňák V. Polymer-supported stereoselective synthesis of tetrahydrobenzopyrazino-thiadiazinone dioxides via N-sulfonyl iminiums. ACS Comb Sci. 2014;16:293–302.
   PubMed Web of Science ®Google Scholar
• Schütznerová E, Oliver AG, Slough GA, et al. Traceless solid-phase synthesis of fused chiral macrocycles via conformational constraint-assisted cyclic iminium formation. Chem Eur J. 2017;23:12876–12885.
   PubMed Web of Science ®Google Scholar
• Nefzi A, Ong AN, Giulianotti AM, et al. Solid phase synthesis of 1,4-benzothiazepin-s-one derivatives. Tetrahedron Lett. 1999;40:4939–4942.
   Web of Science ®Google Scholar
• Meyer JP, Ostresh JM, Nefzi A, et al. Peptides frontiers of peptide science. In: American Peptide Symposia, Peptides as Precursors in the Synthesis of Heterocyclic Positional Scanning Combinatorial Libraries; 2002. p. 25–27.
   Google Scholar
• Morton CG, Salvino JM, Labaudiniere RF, et al. Novel solid-phase synthesis of 1,5-benzothiazepine-4-one derivatives. Tetrahedron Lett. 2000;41:3029–3033.
   Google Scholar
• Ansari LF, Iftikhar F, Haq I, et al. Solid-phase synthesis and biological evaluation of a parallel library of 2,3-dihydro-1,5-benzothiazepines. Bioorg Med Chem. 2008;16:7691–7697.
   PubMedGoogle Scholar
• Fülöpová V, Krchňák V. Solid-phase synthesis of trisubstituted 2,5-dihydrobenzo[f][1,2,5]thiadiazepine 1,1-dioxide derivatives. ACS Comb Sci. 2014;16:412–420.
   PubMed Web of Science ®Google Scholar
• Fulopova V, Krchnakova A, Schutznerova E, et al. Ring contraction of 2,5-dihydrobenzo[f][1,2,5]thiadiazepine 1,1-dioxides: access to 4H-benzo[b][1,4]thiazine 1,1-dioxides. J Org Chem. 2015;80:1795–1801.
   PubMed Web of Science ®Google Scholar
• Souers AJ, Virgilio AA, Rosenquist A, et al. Identification of a potent heterocyclic ligand to somatostatin receptor subtype 5 by the synthesis and screening of beta-turn mimetic libraries. J Am Chem Soc. 1999;121:1817–1825.
   Web of Science ®Google Scholar
• Tymoshenko DO. Nine-membered rings, eight-membered and larger heterocyclic rings and their fused derivatives other seven-membered rings, 2008, Vol. 14, Comprehensive Heterocyclic Chemistry III Editors-in-Chief: Alan R. Katritzky, Christopher A. Ramsden, Eric F.V. Scriven, and Richard J.K. Taylor, ISBN:978-0-08-044992-0.
   Google Scholar
• Souers AJ, Schurer S, Kwack H, et al. Preparation of enantioenriched alpha-bromo acids with diverse side chain functionality. Synthesis (Mass). 1999;4:583–585.
   Google Scholar
• Souers AJ, Ellman JA. Turn mimetic library synthesis: scaffolds and applications. Tetrahedron. 2001;57:7431–7448.
   Web of Science ®Google Scholar
• Virgilio AA, Scurer SC, Ellmann JA. Expedient solid-phase synthesis of putative β-turn mimetics incorporating the i + 1, i + 2, and i + 3 side chains. Tetrahedron Lett. 1996;37:6961–6964.
   Web of Science ®Google Scholar