Solvent-Free Efficient Synthesis of 2,4,5-Triarylimidazolines from Aromatic Aldehydes and Hexamethyldisilazane

Hitoshi Uchida; Takashi Shimizu; Paidi Yella Reddy; Shuichi Nakamura; Takeshi Toru

doi:10.1055/s-2003-39396

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Solvent-Free Efficient Synthesis of 2,4,5-Triarylimidazolines from Aromatic Aldehydes and Hexamethyldisilazane

Hitoshi Uchida^a, Takashi Shimizu^a, Paidi Yella Reddy^b, Shuichi Nakamura^a, Takeshi Toru*^a
^a Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
^b AISIN COSMOS R & D Co., Ltd., 5-50 Hachiken-cho, Kariya, Aichi, 448-8650, Japan
Fax: +81(52)7355217; e-Mail: toru@ach.nitech.ac.jp;

Abstract

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Abstract

A one-step preparation of 2,4,5-triarylimidazolines from aromatic aldehydes was accomplished by heating with hexamethyldisilazane under solvent-free conditions. This reaction provides a convenient preparative method for triarylimidazolines having a variety of aryl groups.

Key words

imidazoline - hexamethyldisilazane - solvent-free - aldehyde - methanediamine

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References

1a Kyrides LP. Zienty FB. Steahly GY. Morrill HL. J. Org. Chem. 1947, 12: 577

1b Hayashi T. Bull. Chem. Soc. Jpn. 1964, 37: 1702

1c Matsuura T. Ito Y. Chem. Lett. 1972, 431

1d Matsuura T. Ito Y. Saito I. Bull. Chem. Soc. Jpn. 1974, 46: 3805

1e Amemiya Y. Miller DD. Hsu F. Synth. Commun. 1990, 20: 2483

1f Campos ME. Jimenez R. Martinez F. Salgado H. Heterocycles 1995, 40: 841

1g Anastassiadou M. Baziard-Mouysset G. Payard M. Synthesis 2000, 1814

For example:

2a Corey EJ. Huang HC. Tetrahedron Lett. 1989, 30: 5235

2b Corey EJ. Imwinkelried R. Pikul SB. J. Am. Chem. Soc. 1989, 111: 5493

2c Corey EJ. Yu CM. Kim SS. J. Am. Chem. Soc. 1989, 111: 5495

2d Corey EJ. DaSilva Jardine P. Virgil S. Yuen PW. Conneell RD. J. Am. Chem. Soc. 1989, 111: 9243

2e Corey EJ. Yu CM. Lee DH. J. Am. Chem. Soc. 1990, 112: 878

2f Zhang W. Loebatch J. Wilson SR. Jacobsen EN. J. Am. Chem. Soc. 1990, 112: 2801

2g Corey EJ. Kim SS. J. Am. Chem. Soc. 1990, 112: 4976

2h Zhang W. Jacobsen EN. J. Org. Chem. 1991, 56: 2296

2i Corey EJ. Imai N. Pikul S. Xiang YB. Tetrahedron Lett. 1991, 32: 7517

2j Corey EJ. Sarshar S. Bordner J. J. Am. Chem. Soc. 1992, 114: 7938

2k Corey EJ. Sarshar S. Lee D.-H. J. Am. Chem. Soc. 1994, 116: 12089

2l Corey EJ. Letavic MA. J. Am. Chem. Soc. 1995, 117: 9616

2m Corey EJ. Sarshar S. Azimioara MD. Newbold RC. Noe MC. J. Am. Chem. Soc. 1996, 118: 7851

2n Evans DA. Nelson SG. J. Am. Chem. Soc. 1997, 119: 6452

3a Fürth A. Monatsh. Chem. 1909, 17: 839

3b Saigo K. Kubota N. Takebayashi S. Hasegawa M. Bull. Chem. Soc. Jpn. 1986, 59: 931

3c Corey EJ. Kühnle FNM. Tetrahedron Lett. 1997, 38: 8631

4a Hunter DH. Sim SK. J. Am. Chem. Soc. 1969, 91: 6202

4b Hunter DH. Sim SK. Can. J. Chem. 1972, 50: 669

4c Hunter DH. Sim SK. Can. J. Chem. 1972, 50: 678

5a Laurent MA. Liebigs Ann. Chem. 1837, 21: 130

5b Kamal A. Ahmad A. Qureshi AA. Tetrahedron 1963, 19: 869

6a Nishiyama K. Saito M. Oba M. Bull. Chem. Soc. Jpn. 1988, 61: 609

6b Grigor’ev SV. Voronkov MG. Mirskov RG. Rakhlin VI. Zh. Obshch. Khim. 2001, 71: 163 ; Russ. J. Gen. Chem. (Engl. Transl.); 2001, 71: 149

7a Reddy PY. Shimizu M. Higashi K. Shimizu T. Toru T. Arkivoc 2001, 8: 111; for online version, see: www.arkat-usa.org

8 Mistryukov EA. Mendeleev Commun. 2001, 29

9 Chen W. Yang F. Zhongguo Yiyao Gongye Zazhi 1993, 24: 280 ; Chem Abstr. 1994, 120, 163554

10 Larter ML. Phillips M. Ortega F. Aguire G. Somanathan R. Walsh PJ. Tetrahedron Lett. 1998, 39: 4785

11 Ogata Y. Kawasaki A. Okumura N. J. Org. Chem. 1964, 29: 1985

12a Sweeley CC. Bentley R. Makita M. Wells WW. J. Am. Chem. Soc. 1963, 85: 2497

12b Cossy J. Pale P. Tetrahedron Lett. 1987, 28: 6039

13 Williams OF. Bailer JC. J. Am. Chem. Soc. 1959, 81: 4464

14 For dihydrochloride, see: Biniecki S. Kabzinska Z. Acta Pol. Pharm. 1970, 27: 327 ; Chem. Abstr. 1971, 74, 99828