Open Access

Diazafluorene in 1,3-Dipolar Cycloaddiction Reactions: Short Review


Cite

[1] Desai J. M., Shah V. H., Synthesis and biological activity of cyanopyridine, isoxazole and pyrazoline derivatives having thymol moiety, Indian J. Chem. 42B/2003, 382–385.10.1002/chin.200322137Search in Google Scholar

[2] Kini S., Gandhi A. M., Novel 2-Pyrazoline Derivatives as Potential Antibacterial and Antifungal Agents, Indian J. Pharm. Sci. 70,1/2008, 105–108.10.4103/0250-474X.40344Search in Google Scholar

[3] Havrylyuk D., Zimenkovsky B., Vasylenko O., Lesyk R., Synthesis and Anticancer and Antiviral Activities of New 2-Pyrazoline-Substituted 4-Thiazolidinones, J. Heterocycl. Chem. 50, S1/2013, E55–E62.10.1002/jhet.1056Search in Google Scholar

[4] Palaska E., Aytemir M., Uzbay I. T., Erol D., Short communication Synthesis and antidepressant activities of some 3, 5-diphenyl-2-pyrazolines, Eur. J. Med. Chem. 36/2001, 539–543.10.1016/S0223-5234(01)01243-0Search in Google Scholar

[5] Rahman M. A., Siddiqui A. A., Pyrazoline Derivatives: A Worthy Insight into the Recent Advances and Potential Pharmacological Activities, Int. J. Pharm. Sci. Drug Res. 2, 3/2010, 165–175.10.4172/2150-3494.1000021Search in Google Scholar

[6] Amir M., Kumar S., Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation, Indian J. Chem. 44/2005, 2532–2537.Search in Google Scholar

[7] Berrocal-Romero J. M., Contijoch-Llobet M. M., Cuberes-Altisent M. R., Frigola-Constansa J., Pyrazoline derivatives, their preparation and application as medicaments, WO 99/62884, 2001.Search in Google Scholar

[8] Nugent R. A., Murphy M., Schlachter S., Dunn C., Smith R. J., Staite N. D., Galinet L., Shields S. K., Aspar D. G., Richard K. A., Rohloff N. A., Pyrazoline bisphosphonate ester as novel antiinflammatory and antiarthritic agents, J. Med. Chem. 36, 1/1993, 134–139.10.1021/jm00053a0178421279Search in Google Scholar

[9] Nugent R. A., Murphy M., Schlachter S. T., Dunn C. J., Smith R. J., Staite, L. A. Galinet N. D., Shields S. K., Aspar D. G., Richard K. A., Rohloff N. A., Pyrazoline bisphosphonate esters as novel antiinflammatory and antiarthritic agents, J. Med. Chem. 36, 1/1993, 134–139.10.1021/jm00053a017Search in Google Scholar

[10] Gomha S. M., Abdallah M. A., Al-Showiman S. S., Morad M. A., Mabkhot Y. N., Synthesis of new pyridopyrimidinone-based thiadiazoles and pyrazolines as potential anti-breast cancer agents, Biomed. Res. 28, 22/2017, 9903–9909.Search in Google Scholar

[11] Durr V. H., Klauck G., Peters K., Von Schnering H. G., Ein neues planares, antiaromatisches Dibenzo[8]annulen, Angew. Chem. 95, 4/1983, 321.10.1002/ange.19830950412Search in Google Scholar

[12] Friscourt F., Fahrni C. J., Boons G. J., Fluorogenic Strain-Promoted Alkyne-Diazo Cycloadditions, Chem. - A Eur. J. 21, 40/20150, 13996–14001.10.1002/chem.201502242471274726330090Search in Google Scholar

[13] Burgert W., Große M., Rewicki D., Gespannte alkyl-aromatische Systeme, 6. 7bH-Indeno[1,2,3-jk] fluorene und 2h-Cyclopenta[jk]fluorene aus Spiroindazolen und -pyrazolen; Regioselektivität einer intramolekularen Cyclisierungsreaktion, Chem. Ber. 115, 1/1982, 309–323.10.1002/cber.19821150128Search in Google Scholar

[14] van Alphen J., Pyrazolines and their rearrangement to form pyrazoles. II. (Pyrazole and pyrazoline derivatives, IV), Recl. Trav. Chim. Pays-Bas, 43/1975, 51–59.Search in Google Scholar

[15] Staudinger H., Gaule A., Diphenylendiazomethan, Berichte der Dtsch. Chem. Gesellschaft, 49, 2/1916, 1951–1960.10.1002/cber.19160490250Search in Google Scholar

[16] Heydt H., Busch K., Regitz M., Untersuchungen an Diazoverbindungen und Aziden, XXXVI. [3 + 2]-Cycloaddition von Diazoalkanen an 1-Cyclopropenyl-phosphinoxide; Isomerisierung der Cycloaddukte, Liebigs Ann. der Chemie, 1980, 4/1980, 590–599.10.1002/jlac.198019800411Search in Google Scholar

[17] Naik A.B., Narwade M., Studies in Influence of Dielectric Constants on Complex Equilibria Between Substituted Pyrazolines and Lanthanide Metal Ions Ph Metrically, Am. J. Sci. Res. 3, 2/2008, 212–216.Search in Google Scholar

[18] Hassenriick K., Hiichstetter H., Martin H., Steigel A., Wingen H., Dipolar Cycloaddition Reactions with heterocyclic Bicyclo[2.2.0] hexenes. A Contribution to the syn-anti Selectivity os cis-3,4-Disubstituted Cuclobutanes, Chem. Ber. 120/1987, 203–212.10.1002/cber.19871200212Search in Google Scholar

[19] Burgert W., Rewicki D., Reaktionen von Spiro[fluoren-9,3′-[3H]pyrazolen] und Spiro[2-cyclopropen-1,9′-fluorenen] mit Nucleophilen, Chem. Ber. 117, 7/1978, 2409–2421.10.1002/cber.19841170712Search in Google Scholar

[20] Shimizu N., Bartlett P.D., Worth F., Cycloaddition of Diazoalkanes to Penta- and hexafluoroacetones. Isolation of A 3-1,3,4-Oxadiazolines and Their Decomposition via Carbonyl Ylides, J. Am. Chem. Soc. 100, 13/1978, 4260–4267.10.1021/ja00481a042Search in Google Scholar

[21] Mlostoń G., Urbaniak K., Linden A, Heimgartner H., A new approach to 2,2-disubstituted 1-(methylsulfanyl)vinyl phosphonates via an intermediate thiocarbonyl ylide, Tetrahedron 65, 39/2009, 8191–8198.10.1016/j.tet.2009.07.074Search in Google Scholar

[22] El-Sawi E.A., Mostafa T.B., Radwan, H.A., Phosphorylation of some new acenaphthenequinone derivatives, Chem. Heterocycl. Compd. 45, 8/2009, 981–989.10.1007/s10593-009-0363-ySearch in Google Scholar

[23] Guo X., Feng L., Wang Q., Li Z., Tao F., 1,3-Dipolar cycloadditions of 9-diazofluorenes and diphenyldiazomethane to 2-acyl-2 H -1,2,3-diazaphospholes, J. Heterocycl. Chem., 43, 2/2006, 353–359.10.1002/jhet.5570430215Search in Google Scholar

[24] Arbuzov B.A., Dianova E.N., Sharipova S.M., Reaction of 2-Phenyl(Acetyl)-5-Methyldiazaphosphole With Diazomethane and Diazofluorene, Bull. Acad. Sci. USSR, Div. Chem. Sci. (English Transl.) 30, 5/1981, 873–876.10.1007/BF00955303Search in Google Scholar

[25] Adam W., Encarnación L.A.A., The synthesis of spiro[adamantane-[1,2]dioxetanes], Chem. Ber. 115, 7/1982, 2592–2605.10.1002/cber.19821150722Search in Google Scholar

[26] Jasiński R., Reakcje 1,3-dipolarnej cykloaddycji: aspekty mechanistyczne i zastosowanie w syntezie organicznej, Radomskie Towarzystwo Naukowe, Radom 2015.Search in Google Scholar

[27] Jasiński R., On the question of zwitterionic intermediates in 1,3-dipolar cycloadditions between hexafluoroacetone and sterically crowded diazocompounds, J. Fluor. Chem. 176, 1/2015, 35–39.10.1016/j.jfluchem.2015.04.020Search in Google Scholar

[28] Mustafa A., Zayed S.M.A.D., Khattab S., Reactions with Diazoalkanes. V. Action of Diazoalkanes and of Aryl Azides on N-Arylmaleimides, J. Am. Chem. Soc. 78, 3/1956, 145–149.10.1021/ja01582a041Search in Google Scholar

[29] Jasiński R., Kula K., Kącka A., Mirosław B., Unexpected course of reaction between (E)-2-aryl-1-cyano-1-nitroethenes and diazafluorene: why is there no 1,3-dipolar cycloaddition?, Monatshefte fur Chemie, 148, 5/2017, 909–915.10.1007/s00706-016-1893-5538701828458402Search in Google Scholar

[30] Vasin V.A., Masterova Y.Y., Razin V.V., Somov N.V., Thermal, acid-catalyzed, and photolytic transformations of spirocyclic 3H-pyrazoles formed by reactions of methyl, phenyl, and p-tolyl phenylethynyl sulfones with 9-diazofluorene, Russ. J. Org. Chem. 50, 9/2014, 1323–1334.10.1134/S1070428014090152Search in Google Scholar