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Diazafluorene in 1,3-dipolar cycloaddiction reactions: short review

Publication date: 25.06.2018

Technical Transactions, 2018, Volume 6 Year 2018 (115), pp. 41 - 53

https://doi.org/10.4467/2353737XCT.18.085.8690

Authors

,
Karolina Kula
Institute of Organic Chemistry and Technology, Cracow University of Technology
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Agnieszka Łapczuk-Krygier
Institute of Organic Chemistry and Technology, Cracow University of Technology
All publications →

Titles

Diazafluorene in 1,3-dipolar cycloaddiction reactions: short review

Abstract

This review is an attempt to systemise knowledge within the field of 1,3DC reactions of diazafluorene with different dipolarophiles. This paper is arranged according to the dipolarophile structure. We are hoping that this review can help organic chemists who deal with the preparation of five-membraned heterocycles. Keywords: diazafluorene, 1,3-dipolar cycloaddition, 1,3-dipol

References

[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.

[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.

[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.

[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.

[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.

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

[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.

[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.

[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]   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.

[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.

[12]   Friscourt F., Fahrni C. J., Boons G. J., Fluorogenic Strain-Promoted Alkyne-Diazo Cycloadditions, Chem. - A Eur. J. 21, 40/20150, 13996–14001.

[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.

[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.

[15]   Staudinger H., Gaule A., Diphenylendiazomethan, Berichte der Dtsch. Chem. Gesellschaft, 49, 2/1916, 1951–1960.

[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.

[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.

[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.

[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.

[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.

[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.

[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.

[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.

[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.

[25]   Adam W., Encarnación L.A.A., The synthesis of spiro[adamantane-[1,2]dioxetanes], Chem. Ber. 115, 7/1982, 2592–2605.

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

[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.

[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.

[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.

[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.

Information

Information: Technical Transactions, 2018, Volume 6 Year 2018 (115), pp. 41 - 53

Article type: Original article

Titles:

Polish:

Diazafluorene in 1,3-dipolar cycloaddiction reactions: short review

English:

Diazafluorene in 1,3-dipolar cycloaddiction reactions: short review

Authors

Institute of Organic Chemistry and Technology, Cracow University of Technology

Institute of Organic Chemistry and Technology, Cracow University of Technology

Published at: 25.06.2018

Article status: Open

Licence: None

Percentage share of authors:

Karolina Kula (Author) - 50%
Agnieszka Łapczuk-Krygier (Author) - 50%

Article corrections:

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Publication languages:

English