Lewis acid catalyzed reaction of cinnamanilides: Competition of intramolecular and intermolecular Friedel-Crafts reaction

Synthesis

Volumn , Issue 1, 1997, Pages 87-90

  Wang, Tai Chi ^a,b   Chen, Yeh Long ^a   Lee, Kuan Han ^b   Tzeng, Cherng Chyi ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b TAJEN INSTITUTE OF TECHNOLOGY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDE; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0031053671     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1505     Document Type: Article

References (12)

1. Preliminary communication: Wang, T.-C.; Chen, Y.-L.; Lee, K.-H.; Tzeng, C.-C. Tetrahedron Lett. 1996, 37, 6369.
2. Fujioka, T.; Teramoto, S.; Mori, T.; Hosokawa, T.; Sumida, T.; Tominaga, M.; Yabuuchi, Y. J. Med. Chem. 1992, 35, 3607.
3. Uno, T.; Ozeki, Y.; Koga, Y.; Chu, G.-N.; Okada, M.; Tamura, K.; Igawa, T.; Unemi, F.; Kido, M.; Nishi, T. Chem. Pharm. Bull. 1995, 43, 1724.
4. Tominaga, M.; Yo, E.; Ogawa, H.; Yamashita, S.; Yabuuchi, Y.; Nakagawa, K. Chem. Pharm. Bull. 1984, 32, 2100.
5. Nishi, T.; Tabusa, F.; Tanaka, T.; Shimizu, T.; Nakagawa, K. Chem. Pharm. Bull. 1985, 33, 1140.
6. Tomigawa, M.; Ogawa, H.; Yo, E.; Yamashita, S.; Yabuuchi, Y.; Nakagawa, K. Chem. Pharm. Bull. 1988, 35, 3699.
7. Chen, Y.-L.; Wang, T.-C.; Lee, K.-H.; Chang, Y.-L.; Teng, C.-M.; Tzeng, C.-C. Helv. Chim. Acta 1996, 79, 651.
8. Chen, Y.-L.; Wang, T.-C.; Liang, S.-C.; Teng, C.-M.; Tzeng, C.-C. Chem. Pharm. Bull. 1996, 44, 1591.
9. Kobayashi, Y.; Kumadaki, I. Chem. Pharm. Bull. 1969, 17, 510.
10. Colonge, J.; Chambard, R. Bull. Soc. Chim. Fr. 1953, 982.
11. Manimaran, T.; Thiruvengadam, T. K.; Ramakrishnan, V. T. Synthesis 1975, 739.
12. Selected bond lengths (Å): C1-C2 1.539(4); C1-C10 1.518(4); C1-C16 1.525(4); C2-C3 1.512(4); N1-C3 1.336(3); N1-C4 1.435(3); O1-C3 1.232(3). Selected bond angles (degree): C1-C2-C3 111.9(2); C1-C10-C11 121.1 (3); C1-C10-C15 120.9(3); C2-C1-C10 111.2(2); C2-C1-C16 112.4(2); C3-N1-C4 129.0(2); C10-C1-C16 112.0(2); N1-C3-C2 115.9(3); N1-C4-C5 115.9(2); N1-C4-C9 124.9(3); O1-C3-C2 120.1(3). Supplementary material: Atomic coordinates, bond lengths and angles, torsion angles and thermal parameters have been deposited at the Crystallographic Center of National Sun Yatsen University.