Imination of sulfoxides using 3-acetoxyaminoquinazolinone as nitrogen source in the presence of hexamethyldisilazane
作者： Semistan Karabuga , Cavit Kazaz , Hamdullah Kilic , Sabri Ulukanli , Ayhan Celik
DOI: 10.1016/J.TETLET.2005.05.109
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摘要: The reaction of 3-acetoxyaminoquinazolinone (QNHOAc) with various sulfoxides in the presence HMDS as an acetic acid scavenger, afforded corresponding sulfoximides good yields. Sulfoximidation phenyl methyl sulfoxide using a Q*NHOAc having stereogenic centre on its 2-position gave products 1.3:1 ratio diastereomers.
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sci-hub.se 参考文章(30)
Dominique Leca, Kai Song, Muriel Amatore, Louis Fensterbank, Emmanuel Lacôte, Max Malacria, Iodine(III)-mediated preparations of nitrogen-containing sulfur derivatives: Dramatic influence of the sulfur oxidation state Chemistry: A European Journal. ,vol. 10, pp. 906- 916 ,(2004) , 10.1002/CHEM.200305525
Carsten Bolm, Guido Moll, Jan D. Kahmann, Synthesis of Pseudopeptides with Sulfoximines as Chiral Backbone Modifying Elements Chemistry: A European Journal. ,vol. 7, pp. 1118- 1128 ,(2001) , 10.1002/1521-3765(20010302)7:5<1118::AID-CHEM1118>3.0.CO;2-3
Y. Tamura, H. Matsushima, J. Minamikawa, M. Ikeda, K. Sumoto, Syntheses and some properties of N-unsubstituted sulfilimines Tetrahedron. ,vol. 31, pp. 3035- 3040 ,(1975) , 10.1016/0040-4020(75)80143-8
Abdullah G Al-Sehemi, Robert S Atkinson, John Fawcett, David R Russell, 3-(N,N-Diacylamino)quinazolin-4(3H)-ones as enantioselective acylating agents for amines Tetrahedron Letters. ,vol. 41, pp. 2239- 2242 ,(2000) , 10.1016/S0040-4039(00)00138-6
Robert S Atkinson, 3-Acetoxyaminoquinazolinones (QNHOAc) as aziridinating agents: ring-opening of N-(Q)-substituted aziridines Tetrahedron. ,vol. 55, pp. 1519- 1559 ,(1999) , 10.1016/S0040-4020(98)01199-5
M. Reggelin, H. Weinberger, V. Spohr, Geminal Bis(sulfoximine)s: Synthesis and Applications in Asymmetric Catalysis Advanced Synthesis & Catalysis. ,vol. 346, pp. 1295- 1306 ,(2004) , 10.1002/ADSC.200404164
Stig Allenmark, Sofia Claeson, Christina Löwendahl, Stereochemistry of the formation of endocyclic sulfoximides from o-carboxyphenyl sulfoxides Tetrahedron-asymmetry. ,vol. 7, pp. 361- 364 ,(1996) , 10.1016/0957-4166(96)00006-7
Robert S. Atkinson, John Fawcett, Ian S. T. Lochrie, Sabri Ulukanli, Thomas A. Claxton, Aziridination of β-substituted styrene derivatives with 3-acetoxyaminoquinazolin-4(3H)-ones: probing transition state geometry from changes in diastereoselectivity Journal of The Chemical Society-perkin Transactions 1. pp. 819- 828 ,(2002) , 10.1039/B107327N
Tung Siu, Andrei K. Yudin, Electrochemical imination of sulfoxides using N-aminophthalimide. Organic Letters. ,vol. 4, pp. 1839- 1842 ,(2002) , 10.1021/OL0257530
Richard W. HEINTZELMAN, Daniel SWERN, Improved Preparation of S,S-Dimethyl-N-arylsulfonylsulfoximines1 Synthesis. ,vol. 1976, pp. 731- 733 ,(1976) , 10.1055/S-1976-24176