Low-Valent Titanium Reagent-Promoted Intramolecular Reductive Coupling Reactions of Ketomalononitriles: A Facile Synthesis of Benzo[4,5]indene, Acridine and Quinoline Derivatives

Daqing Shi; Liangce Rong; Chunling Shi; Qiya Zhuang; Xiangshan Wang; Shujiang Tu; Hongwen Hu

doi:10.1055/s-2005-861820

PAPER

Low-Valent Titanium Reagent-Promoted Intramolecular Reductive Coupling Reactions of Ketomalononitriles: A Facile Synthesis of Benzo[4,5]indene, Acridine and Quinoline Derivatives

Daqing Shi*^a-c, Liangce Rong^a, Chunling Shi^a, Qiya Zhuang^a,b, Xiangshan Wang^a,b, Shujiang Tu^a,b, Hongwen Hu^c
^a Department of Chemistry, Xuzhou Normal University, Xuzhou 221116, P. R. China
^b The Key Laboratory of Biotechnology for Medical Plants of Jiangsu Province, Xuzhou 221116, P. R. China
^c Department of Chemistry, Nanjing University, Nanjing 210093, P. R. China
Fax: +86(516)3403164; e-Mail: dqshi@263.net;

Abstract

All articles of this category

Abstract

The intramolecular reductive coupling reactions of ketomalononitriles induced by a low-valent titanium reagent were studied. Benzo[4,5]indene, acridine and quinoline derivatives are prepared in good yields under neutral and mild conditions.

Key words

low-valent titanium - benzo[4,5]indene - acridine - quinoline

Full Text

References

1 McMurry JE. Chem. Rev. 1989, 89: 1513

2a McMurry JE. Fleming MP. J. Org. Chem. 1976, 41: 896

2b McMurry JE. Acc. Chem. Res. 1983, 16: 405

2c Lenoir D. Synthesis 1989, 883

2d Fürstner A. Bogdanovi B. Angew. Chem., Int. Ed. Engl. 1996, 35: 2443

2e Shi DQ. Chen JX. Chai WY. Chen WX. Kao TY. Tetrahedron Lett. 1993, 34: 2963

2f Shi DQ. Rong LC. Wang JX. Zhuang QY. Wang XS. Hu HW. Tetrahedron Lett. 2003, 44: 3199

2g Shi DQ. Wang JX. Shi CL. Rong LC. Zhuang QY. Hu HW. Synlett 2004, 1098

2h Li J. Shi DQ. Chen WX. Heterocycles 1997, 45: 2381

2i Shi DQ. Shi CL. Wang XS. Zhuang QY. Tu SJ. Hu HW. Synlett 2004, 2239

3 Zhou LH. Shi DQ. Gao Y. Shen WB. Dai GY. Chen WX. Tetrahedron Lett. 1997, 38: 2729

4 Zhou LH. Tu SJ. Shi DQ. Dai GY. Chen WX. Synthesis 1998, 851

5a Chen WX. Zhang JH. Hu MY. Wang XC. Synthesis 1990, 701

5b Chen JX. Jiang JP. Chen WX. Kao TY. Chin. Chem. Lett. 1991, 2: 351

5c Chen JX. Jiang JP. Chen WX. Kao TY. Heterocycles 1990, 701

6 Shi DQ. Zhao H. Wang XS. Yao CS. Zhou LH. J. Chem. Res., Synop. 2002, 452

7 Yamamoto Y. Matsumi D. Itoh K. Chem. Commun. 1998, 875

8 Chen JX. Chen WX. Zhang JH. Chin. J. Org. Chem. 1992, 12: 26

9 Huang LS. Acta Pharm. Simica 1983, 18: 553

10a Huang LS. Acta Pharm. Simica 1983, 18: 633

10b Akira Y. Kazuo K. Radioisotopes 1979, 28: 687

11 Claret PA. In Comprehensive Organic Chemistry Vol. 4: Barton DHR. Ollis WD. Pergamon Press; Oxford: 1979. p.155

12 Jiang JP. Gao J. Shen WB. Chen WX. Acta Chimica Sinica 1992, 50: 1134

13 Shi DQ. Lu ZS. Wang SH. Tu SJ. Dai GY. Synth. Commun. 1998, 28: 4003

14 Kundu NG. Mahanty JS. Das B. Tetrahedron Lett. 1993, 34: 1625