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Articles

[3+2]-Cycloadditions of nitrilimines with heteroaryl thioketones

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Pages 604-613 | Received 19 Apr 2017, Accepted 18 Jun 2017, Published online: 06 Jul 2017

References

  • Caramella P, Grünanger P. Nitrile oxides and imines. In: Padwa A, editor. 1,3-Dipolar cycloaddition chemistry. New York: John Wiley & Sons; 1984. p. 291–392.
  • Sharp JT. Nitrile ylides and nitrile imines. In: Padwa A, Pearson WH, editors. Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products. New York: John Wiley & Sons; 2002. p. 473–537.
  • Toubro NH, Holm A. Nitrilimines. J Am Chem Soc. 1980;102:2093–2094.
  • Meier H, Heinzelmann W, Heimgartner H. Direct detection of diphenylnitrilimine in the photolysis of 2,5-diphenyltetrazole. Chimia. 1980;34:504–506.
  • Bégué D, Qiao GGH, Wentrup C. Nitrile imines: matrix isolation, IR spectra, structures, and rearrangement to carbodiimides. J Am Chem Soc. 2012;134:5339–5350.
  • Réau R, Veneziani G, Dahan F, et al. An easy synthesis of nitrilimine. Crystal structure analysis of a unheteroatom substituted stabilized nitrilimine. Angew Chem Int Ed Engl. 1992;31:439–440.
  • Sicard G, Baceiredo A, Bertrand G. Synthesis and reactivity of a stable nitrile imine. J Am Chem Soc. 1988;110:2663–2664.
  • Granier M, Baceiredo A, Bertrand G. The first direct proof of a nitrilimine-diaza isomerization. Synthesis of a relatively stable N-silylated nitrilimine. Angew Chem Int Ed Engl. 1988;27:1350–1351.
  • Arthur MP, Baceiredo A, Fischer J, et al. Substitution reactions at nitrilimine skeletons. Synthesis. 1992;43–45.
  • Bertrand G, Wentrup C. Nitrile imines: from matrix characterization to stable compounds. Angew Chem Int Ed Engl. 1994;33:527–545.
  • Huisgen R, Fišera L, Giera H, et al. Thiones as superdipolarophiles: rates and equilibra of nitrone cycloadditions to thioketones. J Am Chem Soc. 1995;117:9671–9678.
  • Huisgen R, Grashey R, Seidel M, et al. 1,3-Dipolar addition. III. Reaction of diphenylnitrilimine with carbonyl und thiocarbonyl compounds. Liebigs Ann Chem. 1962;658:169–180.
  • Dunstan JBF, Elsey GM, Russell RA, et al. Dipolar cycloaddition reactions of nitrilimines. Aust J Chem. 1998;51:499–510.
  • Itto MYA, Feddouli A, Boutalib A, et al. Highly diastereoselective cycloaddition of diarylnitrilimines to the C=S bond of (1R)-thiocamphor as a source of chiral spiro-1,3,4-thiadiazoles. J Sulfur Chem. 2013;34:250–258.
  • Katada T, Eguchi S, Sasaki T. Thermal cycloaddition reactions of thiocarbonyl compounds. Part 2. 1,3-Dipolar cycloaddition reactions of adamantanethione with nitrile oxides, nitrilimines, and diazoalkanes. J Chem Soc Perkin Trans 1. 1984;2641–2647.
  • Korchevin NA, Usov VA, Voronkov MG, et al. α,β-Unsaturated sulfur compounds. XX. [2 + 3]-Cycloaddition of 3-amino-2-aryl-1-indenethiones to nitrilium betaines and azidobenzene. Zh Org Khim. 1986;22:1276–1282.
  • Linden A, Awad EMAH, Heimgartner H. A rhodanine derivative and its cycloadduct with diphenyl nitrile imine. Acta Crystallogr Sect C. 1999;55:1877–1881.
  • Caleb AA, Ballo D, Rachid B, et al. Synthesis and antibacterial activity of new spiro[thiadiazoline-quinoxaline] derivatives. Arkivoc. 2011;2011(2):217–226.
  • Mlostoń G, Grzelak P, Hamera-Fałdyga R, et al. Aryl, hetaryl, and ferrocenyl thioketones as versatile building blocks for exploration in the organic chemistry of sulfur. Phosphorus Sulfur Silicon Relat Elem. 2017;192:204–211.
  • Mlostoń G, Urbaniak K, Linden A, et al. Selenophene-2-yl-substituted thiocarbonyl ylides – at the borderline of dipolar and biradical reactivity. Helv Chim Acta. 2015;98:453–461.
  • McKee ML, Mlostoń G, Urbaniak K, et al. Dimerization reactions of aryl selenophen-2-yl-substituted thiocabonyl S-methanides as diradical processes: a computational study. Beilstein J Org Chem. 2017;13:410–416.
  • Grzelak P, Utecht G, Jasiński M, et al. First (3+2)-cycloadditions of thiochalcones as C=S dipolarophiles: efficient synthesis of 1,3,4-thiadiazoles via reactions with fluorinated nitrile imines. Synthesis. 2017;49:2129–2137.
  • Mlostoń G, Urbaniak K, Utecht G, et al. Trifluoromethylated 2,3-dihydro-1,3,4-thiadiazoles via the regioselective [3+2]-cycloadditions of fluorinated nitrile imines with aryl, hetaryl, and ferrocenyl thioketones. J Fluorine Chem. 2016;192:147–154.
  • Dogan HN, Duran A, Rollas S, et al. Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimicrobial activities. Bioorg Med Chem. 2002;10:2893–2898.
  • Hu Y, Li C-Y, Wang X-M, et al. 1,3,4-Thiadiazole. Synthesis, reactions, and applications in medicinal, agricultural, and materials chemistry. Chem Rev. 2014;114:5572–5610.
  • Johnson CK. ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory. Oak Ridge, Tennessee; 1976.
  • Huisgen R, Seidel M, Wallbillich G, et al. Diphenylnitrilimine and its 1,3-dipolar additions to alkenes und alkynes. Tetrahedron. 1962;17:3–29.
  • Spiteri C, Keeling S, Moses JE. New synthesis of 1-substituted-1H-indazoles via 1,3-dipolar cycloaddition of in situ generated nitrile imines and benzyne. Org Lett. 2010;12:3368–3371.
  • Mlostoń G, Pipiak P, Linden A, et al. Studies on the reactions of thiocarbonyl S-methanides with hetaryl thioketones. Helv Chim Acta. 2015;98:462–473.
  • Mlostoń G, Pipiak P, Heimgartner H. Diradical reaction mechanism in [3+2]-cycloadditions of hetaryl thioketones with alkyl- or trimethylsilyl-substituted diazomethanes. Beilstein J Org Chem. 2016;12:716–724.
  • Mlostoń G, Urbaniak K, Gębicki K, et al. Hetaryl thioketones. Synthesis and selected reactions. Heteroatom Chem. 2014;25:548–555.
  • Patel HV, Vyas KA, Pandey SP, et al. Facile synthesis of hydrazonyl halides by reaction of hydrazones with N-halosuccinimide-dimethyl sulfide complex. Tetrahedron. 1996;52:661–668.
  • Ali KA, Ragab EA, Kamal M, et al. Synthetic access to some new benzothiazole-based 1,3,4-thiadiazole and 1,3-thiazole derivatives. Turk J Chem. 2016;40:277–282.
  • CCDC-1544688 and 1544689 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
  • Hooft R. KappaCCD collect software. Delft (The Netherlands): Nonius BV; 1999.
  • Otwinowski Z, Minor W. Chapter. In: Carter Jr CW, Sweet RM, editors. Methods in enzymology, Vol. 276, macromolecular crystallography, Part A. New York: Academic Press; 1997. p. 307–326.
  • Blessing RH. An empirical correction for absorption anisotropy. Acta Crystallogr Sect A. 1995;51:33–38.
  • Sheldrick GM. A short history of SHELX. Acta Crystallogr Sect A. 2008;64:112–122.
  • Maslen EN, Fox AG, O’Keefe MA. In: Wilson AJC, editor. International tables for crystallography. Vol. C. Dordrecht: Kluwer Academic; 1992. Table 6.1.1.1; p. 477–486.
  • Stewart RF, Davidson ER, Simpson WT. Coherent X-ray scattering for the hydrogen atom in the hydrogen molecule. J Chem Phys. 1965;42:3175–3187.
  • Ibers JA, Hamilton WC. Dispersion corrections and crystal structure refinements. Acta Crystallogr. 1964;17:781–782.
  • Creagh DC, McAuley WJ. In: Wilson AJC, editor. International tables for crystallography. Vol. C. Dordrecht: Kluwer Academic; 1992. Table 4.2.6.8. p. 219–222.
  • Creagh DC, Hubbell JH. In: Wilson AJC, editor. International tables for crystallography. Vol. C. Dordrecht: Kluwer Academic; 1992. Table 4.2.4.3. p. 200–206.
  • Sheldrick GM. Crystal structure refinement with SHELXL. Acta Crystallogr Sect C. 2015;71:3–8.

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