An Unusual Synthesis of Tröger’s Bases Using DMSO/HCl as Formaldehyde Equivalent

Zhong Li; Xiaoyong Xu; Yanqing Peng; Zhaoxing Jiang; Chuanyong Ding; Xuhong Qian

doi:10.1055/s-2005-861868

SHORTPAPER

An Unusual Synthesis of Tröger’s Bases Using DMSO/HCl as Formaldehyde Equivalent

Zhong Li*^a,b, Xiaoyong Xu^a, Yanqing Peng^a, Zhaoxing Jiang^a, Chuanyong Ding^a, Xuhong Qian*^b
^a Shanghai Key Lab of Chemistry Biology, Institute of Pesticides and Pharmaceuticals, East China University of Science and Technology, P.O. Box 544,130, Meilong Road Shanghai 200237, P. R. China
^b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, P. R. China
Fax: +86(21)64252603; e-Mail: lizhong@ecust.edu.cn;

Abstract

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Abstract

The reactions between anilines and DMSO/HCl produce Tröger’s bases in moderate yield. The Tröger’s bases bearing an electron-withdrawing group can also be synthesized through this procedure. In this reaction, DMSO/HCl acts as formaldehyde equivalent.

Key words

Tröger’s bases - DMSO/HCl - formaldehyde equivalent

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Referenzen

References

<A NAME="RF18004SS-1">1</A> Tröger J. J. Prakt. Chem. 1887, 36: 225

<A NAME="RF18004SS-2">2</A> Spielman MA. J. Am. Chem. Soc. 1935, 57: 583

<A NAME="RF18004SS-3">3</A> Kubo Y. Ohno T. Yamanaka J. Tokita S. Iida T. Ishimaru Y. J. Am. Chem. Soc. 2001, 123: 12700

<A NAME="RF18004SS-4">4</A> Becker DP. Finnegan PM. Collins PM. Tetrahedron Lett. 1993, 34: 1889

<A NAME="RF18004SS-5">5</A> Wilcox CS. Adrian JC. J. Am. Chem. Soc. 1991, 113: 678

<A NAME="RF18004SS-6">6</A> Jensen J. Tejler J. Wärnmark K. J. Org. Chem. 2002, 67: 6008

<A NAME="RF18004SS-7">7</A> Kobayashi T. Moriwaki T. Tsubakiyama M. Yoshida S. J. Chem. Soc., Perkin Trans. 1 2002, 1963

<A NAME="RF18004SS-8">8</A> Bailly C. Laine W. Demeunynck M. Lhomme J. Biochem. Biophys. Res. Commun. 2000, 273: 681

<A NAME="RF18004SS-9">9</A> Goswami S. Ghosh K. Dasgupta S. J. Org. Chem. 2000, 65: 1907

<A NAME="RF18004SS-10">10</A> Bag BG. Kiedrowski G. Angew. Chem. Int. Ed. 1999, 38: 3713

<A NAME="RF18004SS-11">11</A> Samuel HW. Qi JZ. J. Org. Chem. 1991, 56: 485

<A NAME="RF18004SS-12">12</A> Pardo C. Sesmilo E. Gutierrez-Puebla E. Angeles M. J. Org. Chem. 2001, 66: 1607

<A NAME="RF18004SS-13">13</A> Webb TH. Wilcox CS. J. Org. Chem. 1990, 55: 363

<A NAME="RF18004SS-14">14</A> Bag BG. Maitra U. Synth. Commun. 1995, 25: 1849

<A NAME="RF18004SS-15">15</A> Sucholeiki I. Lynch V. Phan L. Wilcox CS. J. Org. Chem. 1988, 53: 98

<A NAME="RF18004SS-16">16</A> Cerrada L. Cudero J. Elguero J. Pardo C. J. Chem. Soc., Chem. Commun. 1993, 1713

<A NAME="RF18004SS-17">17</A> Mederski WWKR. Baumgarth M. Germann M. Kux D. Weitzel T. Tetrahedron Lett. 2003, 44: 2133

<A NAME="RF18004SS-18">18</A> He HW. Liu ZJ. Huaxue Tongbao 1989, 12: 26 ; Chem. Abstr. 1989, 113, 114730

<A NAME="RF18004SS-19">19</A> Majetich G. J. Org. Chem. 1997, 4321

<A NAME="RF18004SS-20">20</A> Srivastava SK. Chem. Commun. 1996, 2679

<A NAME="RF18004SS-21">21</A> Welch JT. Tetrahedron 1987, 43: 3123

<A NAME="RF18004SS-22">22</A> Jensen J. Wäernmark K. Synthesis 2001, 1873

<A NAME="RF18004SS-23">23</A> Partridge C. J. Chem. Soc. 1955, 991

<A NAME="RF18004SS-24">24</A> Miller W. J. Am. Chem. Soc. 1941, 63: 832