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Synthesis 2015; 47(19): 3036-3042
DOI: 10.1055/s-0034-1380447
DOI: 10.1055/s-0034-1380447
paper
Synthesis of Oxa-aza- and Bis-oxathiaaza[3.3.3]propellanes from Dicyanomethylene-1,3-indanedione and 2,5-Dithiobiureas
Authors
Further Information
Publication History
Received: 17 March 2015
Accepted after revision: 06 May 2015
Publication Date:
07 July 2015 (online)
Abstract
An efficient route for the synthesis of oxa-aza- and bis-oxathiaaza[3.3.3]propellanes via reactions of symmetrical and unsymmetrical N1,N2-disubstituted hydrazine-1,2-dicarbothioamides (2,5-dithiobiureas) with (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile in tetrahydrofuran is described. The rationale behind these conversions involving nucleophilic addition on the dicyanomethylene carbon atom is presented. The structures of these unusual products are confirmed by X-ray crystal structure analysis.
Key words
dicyanomethylene-1,3-indanedione - 2,5-dithiobiureas - oxa-aza[3.3.3]propellane - bis-oxathiaaza[3.3.3]propellanes - N2,N5-disubstituted 1,3,4-thiadiazolesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-34-1380447.
- Supporting Information (PDF) (opens in new window)
-
References
- 1 Wiberg KB. Chem. Rev. 1989; 89: 975
- 2 Hopf H. Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives. Wiley-VCH; Weinheim: 2000
- 3 Eliel EL, Wilen SH, Mander LN. Stereochemistry of Organic Compounds . John Wiley & Sons; New York: 1994
- 4 Miao MZ, Cao J, Zhang JJ, Huang X, Wu LL. J. Org. Chem. 2013; 78: 2687
- 5 Zhang LJ, Yan CG. Tetrahedron 2013; 69: 4915
- 6 Jansone-Popova S, May JA. J. Am. Chem. Soc. 2012; 134: 17877
- 7 Rezvanian A, Alizadeh A, Zhu LG. Synlett 2012; 23: 2526
- 8 Asahi K, Nishino H. Tetrahedron 2008; 64: 1620
- 9 Almog J, Stepanov N, Dubnikova F. Tetrahedron Lett. 2008; 49: 1870
- 10 Osawa E, Yonemitsu O. Carbocyclic Cage Compounds: Chemistry and Applications. VCH; Weinheim: 1992: 125
- 11 Sugimoto Y, Babiker HA. A, Saisho T, Furumoto T, Inanaga S, Kato M. J. Org. Chem. 2001; 66: 3299
- 12 Yu B.-W, Chen J.-Y, Wang Y.-P, Cheng K.-F, Li X.-Y, Qin G.-W. Phytochemistry 2002; 61: 439
- 13 Lagona J, Mukhopadhyay P, Chakrabarti S, Isaacs L. Angew. Chem. Int. Ed. 2005; 44: 4844
- 14 Kim K, Selvapalam N, Ko YH, Park KM, Kim D, Kim J. Chem. Soc. Rev. 2007; 36: 267
- 15 Keshavarz MH. J. Hazard. Mater. 2007; 141: 536
- 16 Shin M, Kim MH, Ha TH, Jeon J, Chung KH, Kim JS, Kim YG. Tetrahedron 2014; 70: 1617
- 17 Ortíz A, Carrasco J, Höpfl H, Santillan R, Farfán N. Synth. Commun. 1998; 28: 1293
- 18 Yamamoto N, Fujii H, Nemoto T, Nakajima R, Momen S, Izumimoto N, Hasebe K, Mochizuki H, Nagase H. Bioorg. Med. Chem. Lett. 2011; 21: 4104
- 19 Nagase H, Akiyama J, Nakajima R, Hirayama S, Nemoto T, Gouda H, Hirono S, Fujii H. Bioorg. Med. Chem. Lett. 2012; 22: 2775
- 20 Fujii H, Nakajima R, Akiyama J, Yamamoto N, Hirayama S, Nemoto T, Gouda H, Hirono S, Nagase H. Bioorg. Med. Chem. Lett. 2012; 22: 7697
- 21 Weiss U, Edwards JM. Tetrahedron Lett. 1968; 9: 4885
- 22 Kotha S, Chinnam AK, Tiwari A. Beilstein J. Org. Chem. 2013; 9: 2709
- 23 Weinberg O, Knowles P, Ginsburg D. Helv. Chim. Acta 1985; 68: 610
- 24 Yavari I, Malekafzali A, Skoulika S. Tetrahedron Lett. 2014; 55: 3154
- 25 Rezvanian A, Alizadeh A. Tetrahedron 2012; 68: 10164
- 26 Alizadeh A, Bayat F, Zhu LG. Aust. J. Chem. 2014; 67: 949
- 27 Alizadeh A, Bayat F. Helv. Chim. Acta 2014; 97: 694
- 28 Hassan AA, Nour El-Din AM, Abdel-Latif FF, Mostafa SM, Bräse S. J. Chem. Res. 2010; 493
- 29 Hassan AA, Nour El-Din AM, Abdel-Latif FF, Mostafa SM, Bräse S. Chem. Pap. 2012; 66: 295
- 30 Hassan AA, Ibrahim YR, El-Sheref EM, Abdel-Hamid MA, Bräse S. J. Heterocycl. Chem. 2015; in press; DOI: 10.1002/jhet.2240
- 31 Döpp D, Jüschke S, Henkel G. Z. Naturforsch. B 2002; 57: 460
- 32 Charistos DA, Vagenas GV, Tzavellas LC, Tsoleridis CA, Rodios NA. J. Heterocycl. Chem. 1994; 31: 1593
- 33 Gewald K, Schindler R. J. Prakt. Chem. 1990; 332: 223
- 34 Kalinowski H.-O, Berger S, Braun S. 13C-NMR-Spektroskopie . Georg Thieme Verlag; Stuttgart: 1984
- 35 Kepe V, Požgan F, Golobič A, Polanc S, Kočevar M. J. Chem. Soc., Perkin Trans. 1 1998; 2813
- 36 Mizrakh LT, Polanskaya LYu, Gvozdetskii AN, Vosil’ev AM, Ivanova TM, Lisina NI. S. Khim. Farm. Zh. 1987; 21: 322 ; Chem. Abstr. 1988, 108, 21771r
- 37 Silberg A, Simiti I, Cosma N, Proinov I. Acad. Rep. Pop. Rom. Filiala Cluj, Studi Cercetavdri Chim. 1957; 8: 315 ; Chem. Abstr. 1961, 55, 17626e
- 38 Bazavova IM, Dubenko RG, Shevchenko LI, Pel’kis PS. Ukr. Khim. Zh. (Russ. Ed.) 1980; 46: 286 ; Chem. Abstr. 1980, 93, 71237p
- 39 Udo E, Johannes D. DD 86815, 1972 ; Chem. Abstr. 1973, 78, 11063f.
- 40 Chatterjee S. J. Chem. Soc. B 1969; 725
- 41 Yella R, Khatun N, Rout SK, Patel BK. Org. Biomol. Chem. 2011; 9: 3235
- 42a Eggensperger H, Berscheid R. SOFW J. 1994; 120: 286 ; Chem. Abstr. 1996, 124, 55859w
- 42b Eggensperger H, Berscheid R. SOFW J. 1994; 120: 289 ; Chem. Abstr. 1996, 124, 55859w
- 43 Hassan AA, Mourad AE, El-Shaieb KM, Abou-Zied AH, Döpp D. Heteroat. Chem. 2003; 14: 535
- 44 Shen T.-Y, Clark RL, Pessolano AA. ZA7503527, 1976 ; Chem. Abstr. 1977, 86, 72662r.
- 45 Hassan AA, Mohamed NK, Makhlouf MM, Bräse S, Nieger M. Synthesis 2014; 46: 3097
- 46 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
- 47 Crystallographic data (excluding structure factors) for the structure reported in this work have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 1034843 (7). Copies of the data can be obtained free of charge on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk.