Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(2): 199-204
DOI: 10.1055/s-0032-1316830
DOI: 10.1055/s-0032-1316830
paper
Synthesis of 1-Amino-2,5-dihydro-1H-phosphole 1-Oxides and Their N-Phosphinoyl Derivatives, Bis(2,5-dihydro-1H-phosphol-1-yl)amine P,P′-Dioxides
Further Information
Publication History
Received: 29 October 2012
Accepted after revision: 29 November 2012
Publication Date:
12 December 2012 (online)
Abstract
Depending on the molar ratio of the reactants and on the order of mixing, the reactions of a series of primary amines with 1-chloro-2,5-dihydro-1H-phosphole 1-oxides prepared in situ from the corresponding hydroxy-dihydrophosphole oxides afforded 1-amino-2,5-dihydro-1H-phosphole 1-oxides, or their N-phosphinoyl derivatives, bis(2,5-dihydro-1H-phosphol-1-yl)amine P,P′-dioxides. The latter family of P-heterocycles could also be synthesized by the reaction of 1-amino-2,5-dihydro-1H-phosphole oxides with chloro-dihydrophosphole oxides.
-
References
- 1 Quin LD. The Heterocyclic Chemistry of Phosphorus: System Based on the Phosphorus–Carbon Bond. Wiley; New York: 1981: 30
- 2 Quin LD In Comprehensive Heterocyclic Chemistry II. Vol. 2. Katritzky AR, Rees CW, Scriven EF. V. Pergamon/Elsevier; Oxford: 1996. Chap. 2.15, 826
- 3 Phosphorus–Carbon Heterocyclic Chemistry: The Rise of a New Domain. Mathey F. Pergamon; Amsterdam: 2001: 195
- 4 Quin LD. A Guide to Organophosphorus Chemistry. Wiley & Sons; New York: 2000: 249
- 5 Bodalski R, Pietrusiewicz KM, Koszuk J. Tetrahedron 1975; 31: 1907
- 6 Pakulski Z, Kwiatosz R, Pietrusiewicz KM. Tetrahedron Lett. 2003; 44: 5469
- 7 Pakulski Z, Kwiatosz R, Pietrusiewicz KM. Tetrahedron 2005; 61: 1481
- 8 Pakulski Z, Koprowski M, Pietrusiewicz KM. Tetrahedron 2003; 59: 8219
- 9 Pakulski Z, Pietrusiewicz KM. Tetrahedron: Asymmetry 2004; 15: 41
- 10 Haritha B, Reddy VK, Oshikawa T, Yamashita M. Tetrahedron Lett. 2004; 45: 1923
- 11 Yamada M, Yamashita M, Suyama T, Yamashita J, Asai K, Niimi T, Ozaki N, Fujie M, Maddali K, Nakamura S, Ohnishi K. Bioorg. Med. Chem. Lett. 2010; 20: 5943
- 12 Reddy VK, Haritha B, Oshikawa T, Yamashita M. Tetrahedron Lett. 2004; 45: 2851
- 13 Yamashita M, Reddy VK, Reddy PM, Kato Y, Haritha B, Suzuki K, Takahashi M, Oshikawa T. Tetrahedron Lett. 2003; 44: 3455
- 14 Keglevich G. Synthesis 1993; 931
- 15 Keglevich G. Rev. Heteroat. Chem. 1996; 14: 119
- 16 Keglevich G, Tőke L. Trends Org. Chem. 1993; 4: 245
- 17 Keglevich G. Curr. Org. Chem. 2006; 10: 93
- 18 Keglevich G. Top. Heterocycl. Chem. 2009; 20: 65
- 19 Kollár L, Keglevich G. Chem. Rev. 2010; 110: 4257
- 20 Kerényi A, Kovács V, Körtvélyesi T, Ludányi K, Drahos L, Keglevich G. Heteroat. Chem. 2010; 21: 63
- 21 Keglevich G, Bagi P, Szöllősy Á, Körtvélyesi T, Pongrácz P, Kollár L, Drahos L. J. Organomet. Chem. 2011; 696: 3557
- 22 Novák T, Schindler J, Ujj V, Czugler M, Fogassy E, Keglevich G. Tetrahedron: Asymmetry 2006; 17: 2599
- 23 Novák T, Ujj V, Schindler J, Czugler M, Kubinyi M, Mayer ZA, Fogassy E, Keglevich G. Tetrahedron: Asymmetry 2007; 18: 2965
- 24 Ujj V, Schindler J, Novák T, Czugler M, Fogassy E, Keglevich G. Tetrahedron: Asymmetry 2008; 19: 1973
- 25 Jablonkai E, Drahos L, Drzazga Z, Koprowski M, Pietrusiewicz KM, Keglevich G. Heteroat. Chem. 2012; DOI: 10.1002/hc.21047
- 26 Zablocka M, Boutonnet F, Igau A, Dahan F, Majoral JP, Pietrusiewicz KM. Angew. Chem. Int. Ed. 1993; 32: 1735
- 27 Pietrusiewicz KM, Flis A, Ujj V, Körtvélyesi T, Drahos L, Pongrácz P, Kollár L, Keglevich G. Heteroat. Chem. 2011; 22: 730
- 28 Quin LD, Szewczyk J. Phosphorus Sulfur Relat. Elem. 1984; 21: 161
- 29 Keglevich G, Kovács A, Tőke L, Újszászy K, Argay G, Czugler M, Kálmán A. Heteroat. Chem. 1993; 4: 329
- 30 Keglevich G, Dvorszki J, Ujj V, Ludányi K. Heteroat. Chem. 2010; 21: 271
- 31 Quin LD, Bourdieu C, Quin GS. Phosphorus, Sulfur, Silicon Relat. Elem. 1991; 63: 349
- 32 Arbuzov BA, Vizel AO, Zvelreva MA, Studentsova IA, Zaraev RS. Russ. Chem. Bull. 1966; 15: 1786
- 33 Maier L, Diel PJ. Phosphorus, Sulfur, Silicon Relat. Elem. 1996; 115: 273
- 34 Szewczyk J, Lloyd JR, Quin LD. Phosphorus Sulfur Relat. Elem. 1984; 21: 155
- 35 Weissman SA, Baxter SG. Tetrahedron Lett. 1990; 31: 819
- 36 Kenn M, Jansen W, Schmitz-DuMont O. Z. Anorg. Allg. Chem. 1979; 452: 176
- 37 Haritha B, Krishna Reddy V, Takahashi M, Yamashita M. Tetrahedron Lett. 2004; 45: 5339
- 38 Hetherington L, Greedy B, Gouverneur V. Tetrahedron 2000; 56: 2053
- 39 Quin LD, Mesch KA, Bodalski R, Pietrusiewicz KM. Org. Magn. Res. 1982; 20: 83