Low-valent titanium induced novel reductive cyclizations of α,β- unsaturated nitrile compounds

Synthesis

Volumn , Issue 6, 1998, Pages 851-854

  Zhou, Long Hu ^a   Tu, Shu Jiang ^a   Shi, Da Qin ^a   Dai, Gui Yuan ^a   Chen, Wei Xing ^b  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

2 aminoquinolines; Cyclopentenes; Low valent titanium; Reductive cyclization; , unsaturated nitriles

Indexed keywords

2 AMINOQUINOLINE; CYCLOPENTENE DERIVATIVE; NITRILE; TITANIUM; TITANIUM DERIVATIVE; ZINC;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; DIMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0031800165     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2082     Document Type: Article

References (13)

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2. Lenoir, D. Synthesis 1989, 883.
3. Zhou, L. H.; Shi, D. Q.; Gao, Y.; Shen, W. B.; Dai, G. Y.; Chen, W. X. Tetrahedron Lett. 1997, 38, 2729.
4. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
5. Chen, W. X.; Zhang, J. H.; Hu, M. Y.; Wang, X. C. Synthesis 1990, 701.
6. Chen, J. X.; Jiang, J. P.; Chen, W. X.; Kao, T. Y. Heterocycles 1991, 32, 2339.
7. Bartell, L. S.; Roth, E. A.; Hollowell, C. D.; Kuchitsu, K.; Young, J. E. J. Chem. Phys. 1965, 42, 2683.
8. Ammon, H. L.; Mazzochi, P. H.; Regan, M. C.; Colicelli, E. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 1989, C45, 1722.
9. Tyler, J. M. J. Chem. Soc. 1955, 203.
10. Sheldrick, G. M. SHELXS-86, In Crystallographic Computing 3; Sheldrick, G. M., Kruger, C.; Goddard, R. Eds.; Oxford University Press: Oxford, 1986; p 175.
11. Beurskens, P. T.; Admiral, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. DIRDIF-92, The DIRDIF Program System, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1992.
12. TEXSAN:Crystal Structure Analysis Package,Molecular Structural Corporation, 1985 & 1992.
13. Selected bond lengths(Å): N1-C9 1.350(5); C9-C10 1.359(5); C10-C22 1.445(5); C10-C11 1.520(5); C11-C13 1.516(5); C7-C11 1.551(5);C6-C7 1.511(5); C7-C8 1.580(5); C8-C9 1.524(5); C8-C12 1.479(6); C8-C19 1.526(6). Selected bond angles (°): C6-C7-C8 114.1(3); C6-C7-C11 117.1(3); C8-C7-C11 104.2(3); C7-C8-C9 102.2(3); C7-C8-C12 112.3(3); C7-C8-C19 109.9(3); C9-C8-C12 108.1(3); C9-C8-C19 115.8(3); C12-C8-C19 108.6(3); N1-C9-C8 120.0(3); N1-C9-C10 129.4(4); C8-C9-C10 110.2(3); C9-C10-C11 112.6(3); C9-C10-C22 122.4; C11-C10-C22 124.7(3); C7-C11-C10 102.3(3); C7-C11-C13 121.1(3); C10-C11-C13 114.1(3). Supplementary material: Atomic coordinates, bond lengths and angles, torsion angles and thermal parameters have been deposited at the Crystallographic Center of Shanghai Institute of Organic Chemistry.