Chemistry of 2-cyanomethylene-4-thiazolidinone

References

• Jain AK, Vaidya A, Ravichandran V, et al. Recent developments and biological activities of thiazolidinone derivatives: a review. Bioorg Med Chem. 2012;20:3378–3395.
   PubMed Web of Science ®Google Scholar
• Tripathi AC, Gupta SJ, Fatima GN, et al. 4-Thiazolidinones: the advances continue. Eur J Med Chem. 2014;72:52–77.
   PubMed Web of Science ®Google Scholar
• Ottona R, Maccari R, Barreca ML, et al. 5-Arylidene-2-imino-4-thiazolidinones: design and synthesis of novel anti-inflammatory agents. Bioorg Med Chem. 2005;13:4243–4252.
   PubMed Web of Science ®Google Scholar
• Mashrai A, Dar AM, Mir S, et al. Strategies for the synthesis of thiazolidinone heterocycles. Med Chem. 2016;6(4):280–291.
   Google Scholar
• Kapoor G, Pathak D, Bhutani PR, et al. Thiazolidinone as a pharmacologically active molecule. J Chem Pharm Res. 2016;8(4):151–168.
   Google Scholar
• Satzinger G. Substituted 2-methylene-4-thiazolidones. Liebigs Ann Chem. 1963;665:150–165; Chem Abstr. 1963;59:11466f.
   Google Scholar
• Satzinger G. Thiazolidin-4-one derivatives. Ger. 1,150,985 (Cl. C071d), July 4, 1963; US Appl. Mar. 6, 1961; Chem Abstr. 1961;60:528a.
   Google Scholar
• Isidor JL, Mckee RL. Synthesis of 2-methylene-4-thiazolidinones. J Org Chem. 1973;39(20):3615–3617.
   Web of Science ®Google Scholar
• Elnagdi MH, Elmoghagar MRH, Hammam AG. The reaction of malononitrile with thioglycolic acid. A novel procedure for the synthesis of thiazolone derivatives. J Heterocyclic Chem. 1979;16:1541–1543.
   Web of Science ®Google Scholar
• Satzinger G. Heterocycles by reaction of mercapto- and hydroxy carboxylic esters with activated nitriles. Liebigs Ann Chem. 1978:473–511.
   Google Scholar
• Satzinger G. 2-Cyanomethylene-4-thiazolidinone. US 3,193,558 (Cl. 260–306.7), July 6, 1965; Appl. May 31, 1963; Chem Abst. 1965;63:9950b.
   Google Scholar
• Ceder O, Stenhede U. On the structure of 2-methylenethiazolidin-4-ones. Acta Chem Scand. 1973;27(6):1923–1938.
   Google Scholar
• Tverdokhlebov AV, Resnyanska EV, Tolmachev AA, et al. A novel approach to pyrrolo[2,1-b]thiazoles. Synthesis (Mass). 2003;17:2632–2638.
   Web of Science ®Google Scholar
• Shams HZ, Khalifa FA, Barosoum BN, et al. Synthesis and spectroscopic studies on some dyes of the type dihydrazono-2-cyanomethyl-2-thiazolin-4-one. Bull Chem Soc France. 1989;119–122.
   Google Scholar
• Ibrahim MKA. Reactions with heterocyclic diazonium salts: synthesis of several new thiazolo[2,3-c]as triazine- and thiazolo[2,3-c][1,2,4]triazole derivatives. Phosphorus, Sulfur Silicon. 1990;47:61–65.
   Web of Science ®Google Scholar
• El-Rady EA. Novel synthesis of 2-amino[1,4,5]benzoxadiazepine derivatives via mild one-pot reaction. J Heterocyclic Chem. 2002;39:1109–1110.
   Web of Science ®Google Scholar
• Elgemeie GH, Elfahham HA, Hassan SM, et al. Activated nitriles in heterocyclic synthesis: the reaction of nitriles with mercapto acids. Z Naturforsch. 1983;38b:781–785.
   Google Scholar
• Elmoghagar MRH, El-Agamey AA, Abdel-Samad MY, et al. Activated nitrile in heterocyclic synthesis. Part III. Synthesis of N-amino-2-pyridone, pyranopyrazole and thiazolo-pyridine derivatives. J Heterocyclic Chem. 1984;21:1885–1887.
   Web of Science ®Google Scholar
• El-Hag Ali GAM, Khalil A, Ahmed AHA, et al. Studies on thiazolopyridines. Part 2. Synthesis and antimicrobial activity of novel thiazolo[3,2-a]pyridine and thiazolo[3,2-a] [1,8]naphthyridine derivatives having two different aryl moiety. Acta Chem Slov. 2002;49:365–376.
   Web of Science ®Google Scholar
• Azab ME, El-Hag Ali GAM, Abd El-Wahab AHF. Studies on thiazolopyridines. A novel synthesis of bis-thiazolopyridines as promising antimicrobial agent. Acta Pharm. 2003;53:213–221.
   PubMedGoogle Scholar
• El-Gaby MSA, Khafagy MM, El-Hag Ali GAM, et al. Studies on thiazolopyridines. Part 4: Synthesis of hitherto unknown 1,4-bis(thiazolopyridine)benzene derivatives. Phosphorus, Sulfur Silicon. 2003;178:1681–1688.
   Web of Science ®Google Scholar
• Lamphon RQ, El-Gaby MSA, Khafagy MM, et al. Studies on thiazolo-pyridines. Part 5: Synthesis of hitherto unknown thiazolinone and thiazolo[3,2-a]pyridine derivatives having in their structure the morpholin-4-ylmoiety. Phosphorus, Sulfur Silicon. 2004;179:1279–1292.
   Web of Science ®Google Scholar
• Hussein AM, El-Adasy AA, Hafiz ISA, et al. Biological evaluation of some novel thiazole, thiazolo-[3,2-a]pyridine and thiazolo[3′,2′:1,6]pyrido[2,3-d]pyrimidine derivatives containing diphenyl sulfide moiety as antimicrobial agents. J App Pharm. 2014;6(3):296–307.
   Google Scholar
• El-Emary TL, Khalil A, El-Hag Ali GAM, et al. A facile synthesis of some new thiazolo[3,2-a]pyridines containing pyrazolyl moiety and their antimicrobial activity. Phosphorus, Sulfur Silicon. 2005;180:19–30.
   Web of Science ®Google Scholar
• El-Hag Ali GAM, Abd El-Rahman MT, Helal MHM, et al. Novel synthesis of pyrano[2,3-d]thiazole, thiazolo[3,2-a]- pyridine and pyrazolo[3′,4′:4,5]thiazolo[3,2-a]pyridine derivatives. Phosphorus, Sulfur Silicon. 2008;183:3023–3036.
   Web of Science ®Google Scholar
• Hussein EM. One-pot, three-component, green synthesis of some indeno[2′,3′:5,6]pyrido[2,1-b]benzothiazoles and indeno[2′,3′-e]-thiazolo[3,2-a]pyridines. Heterocyclic Lett. 2012;2(1):19–26.
   Google Scholar
• Zaky OS, Moustafa MS, Selim MA, et al. Scope and limitations of a novel synthesis of 3-arylazo-nicotinates. Molecules. 2012;17:5924–5934.
   PubMed Web of Science ®Google Scholar
• Wardakhan WW, Ibrahim DA, Zaki MY. Utility of 2-(4,5-dihydro-4-oxothiazol-2-yl)acetonitrile in the synthesis of fused heterocyclic derivatives with antitumor activities. Heterocycl Commun. 2011;17(3–4):155–160.
   Web of Science ®Google Scholar
• Shmeiss NAMM, Ismail MMF, Soliman AM, et al. Synthesis of novel 1-substituted and 1,9-disubstituted-1,2,3,4-tetrahydro-9H-carbazole derivatives as potential anticancer agents. Molecules. 2000;5:1101–1112.
   Web of Science ®Google Scholar
• Khalifa FA, Ried BY, Hafez FH. Synthesis of fused azoles: synthesis of several new pyrrolo[2,3:4′,5′]pyrrolo[2,1-b]thiazoles and thiazolo[2,3-a]pyridine derivatives. Heterocycles. 1983;20(6):1021–1025.
   Web of Science ®Google Scholar
• Mahmoud MR, Soliman EA, Ibrahim GA, et al. Utility of β-(3,4-dichlorobenzoyl)-α-(phenylthio)propionic acid in heterocyclic synthesis. Phosphorus, Sulfur Silicon. 1998;139:97–106.
   Web of Science ®Google Scholar
• Salem MAI, Soliman EA, Smith MB, et al. Utility of 1-(2,4-dimethoxyphenyl)-3-aryl-prop-2-ene-1-ones as ring transformer in preparing heterocyclic compounds and their potential biological activities. Phosphorus, Sulfur Silicon. 2004;179:61–76.
   Web of Science ®Google Scholar
• Kambe S, Saito K, Sakurai A, et al. Synthetic studies using α,β-unsaturated nitriles: facile synthesis of pyridine derivatives. Synthesis. 1981;531–533.
   Web of Science ®Google Scholar
• El-Moghagar MRH, Ibraheim MKA, Elghandour AHH, et al. A novel synthesis of thiazolo[2,3-d]pyridine derivatives. Synthesis. 1981;635–637.
   Google Scholar
• Sadek KU, Hafez EA, Mourd AE, et al. Activated nitriles in heterocyclic synthesis: The reaction of substituted cinnamonitriles with 2-functionally substituted methyl-2-thiazolin-4-one derivatives. Z Naturforsch. 1984;39b:824–828.
   Google Scholar
• Osman SA, Elgemeie GH, Nawar GA, et al. Activated nitriles in heterocyclic synthesis: synthesis of 6-thiophen-2-yl and 6-furan-2-yl-thiazolo[2,3-a]pyridine derivatives. Monatshefte für Chemie. 1986;117:105–110.
   Web of Science ®Google Scholar
• Elnagdi MH, El-Moghagar MRH, Hafez HA, et al. The reaction of thioglycolic acid with α,β-unsaturated nitriles. a new route for the synthesis of 7H-thiazolo[2,3-a]pyridines. Phosphorus, Sulfur Silicon. 1989;9(3):109–122.
   Google Scholar
• Abdel-Latif FF, Mohammed YS, Abdel-Ghani H, et al. Synthesis through reactions of nucleophiles with acrylonitriles. Part 13: a direct one-pot synthesis of thiazolo-pyridines. Phosphorus, Sulfur Silicon. 1993;78:251–256.
   Web of Science ®Google Scholar
• El-Maghraby AA, El-Hag Ali GAM, Ahmed AHA, et al. Studies on thiazolopyridines. Part 1: antimicrobial activity of some novel fluorinated thiazolo[3,2-a]pyridines and thiazolo[2′,3′:1,6]- pyrido[2,3-d]pyrimidines. Phosphorus, Sulfur Silicon. 2002;177:293–302.
   Web of Science ®Google Scholar
• Mahmoud MR, El-Bordany EAA, Hassan NF, et al. Utility of nitriles in synthesis of pyrido[2,3-d]pyrimidines, thiazolo-[3,2-a]pyridines, pyrano[2,3-b]benzopyrrole and pyrido[2,3-d]-benzopyrroles. Phosphorus, Sulfur Silicon. 2007;18:2507–2521.
   Web of Science ®Google Scholar
• Al-Thebeiti MS. Synthesis of some new thiazolo[3,2-a]pyridines and related heterocyclic systems. IL Farmaco. 2000;55:108–118.
   Google Scholar
• Boominathan M, Nagaraj M, Maheshwaran C, et al. One-pot synthesis of thiazolo[3,2-a]pyridine derivatives via Tandem cyclization in aqueous media. J Heterocyclic Chem. 2014;51:244–248.
   Web of Science ®Google Scholar
• Pemawat G, Talesard GL. Synthesis of ethoxyphthalimido derivatized thiazolodihydro pyridines assembled with pyrazole and isoxazole systems from common intermediate chalcone and evaluation of their antibacterial activity. Ind J Chem. 2011;50B:1173–1180.
   Google Scholar
• Abd El-Latif FM, El-Ready EA, Döpp D. Facile one-pot syntheses of new polyfunctional pyrazolyl substituted and pyrazolo fused pyridines. J Heterocyclic Chem. 2003;40:57–60.
   Web of Science ®Google Scholar
• Abdel Hafiz IS, Rashad ME, Mahfouz MA, et al. Synthesis of new substituted 1,3-diphenyl-5-chloropyrazoles. J Chem Res. 1998(S);690–691: (M):2946–2957.
   Google Scholar
• Abdelrazek FM, Michael FA, Mohamed AE. Synthesis and molluscicidal activity of some 1,3,4-triaryl-5-chloropyrazole, pyrano[2,3-c]pyrazole, pyrazolylphthalazine and pyrano[2,3-d]-thiazole derivaties. Arch Pharm Chem Life Sci. 2006;339:305–312.
   PubMed Web of Science ®Google Scholar
• Elagamey AA, El-Taweel FA, Amer FA, et al. Reactions with 4-(cyanoacetyl)phenazone: synthesis of novel thiazole, hydrazinopyrazole and pyrazolo[5,1-c] [1,2,4]triazine derivatives. Arch Pharm. (Weinheim) 1987;320:246–252.
   Web of Science ®Google Scholar
• Mortikov VYu, Rodinovskaya LA, Fedorov AE, et al. Synthesis of heterocyclic compounds from 4-formyl-pyrazoles. Russian Chem Bull, Int Ed. 2014;63(2):443–456.
   Google Scholar
• Allam YA, Swellem RH, Nawwar GA. Cyanoacetylurea in heterocyclic synthesis: a simple synthesis of heterocyclic condensed uracils. J Chem Res. 2001;(S):346–348.
   Google Scholar
• El-Sakka IA, Zeid IF, Abdel-Bary HM, et al. Reaction with thiaxanthen-9-ol: new thiaxanthene derivatives with molluscicidal and nematocidal activity. Arch Pharm (Weinheim). 1994;327:133–135.
   PubMed Web of Science ®Google Scholar