Synthesis of 2-aryl-2H-[1,2,4]triazoloquinolin-3-one and 2-aryl-2H-[1,2,4]triazoloisoquinolin-3-one derivatives from α-chloroformylarylhydrazines hydrochloride

Tetrahedron

Volumn 66, Issue 4, 2010, Pages 930-934

  Huang, Jiann Jyh ^b   Chen, Kun Lung ^c   Lin, Yu Shiang ^b   Yang, Sheng Chuan ^b   Chuang, Shih Hsien ^b   Chiang, Kuo Chen ^c   Tseng, Wen Che ^a   Wong, Fung Fuh ^a   Yeh, Mou Yung ^c  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b DEVELOPMENT CENTER FOR BIOTECHNOLOGY   (Taiwan)

^c NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

Chloroformylarylhydrazine hydrochloride; Quinoline; Triazoloisoquinolin 3 one; Triazoloquinolin 3 one

Indexed keywords

2 (P CHLOROPHENYL) 2H [1,2,4]TRIAZOLO [3,4 A]ISOQUINOLIN 3 ONE; 2 (P CHLOROPRENE) 2H [1,2,4]TRIAZOLO [4,3 A]QUINOLIN 3 ONE; 2 (P FLUOROPHENYL) 2H [1,2,4]TRIAZOLO [3,4 A]ISOQUINOLIN 3 ONE; 2 (P FLUOROPHENYL) 2H [1,2,4]TRIAZOLO [4,3 A]QUINOLIN 3 ONE; 2 (P METHYLPHENYL) 2H [1,2,4]TRIAZOLO [3,4 A]ISOQUINOLIN 3 ONE; 2 (P METHYLPHENYL) 2H [1,2,4]TRIAZOLO [4,3 A]QUINOLIN 3 ONE; 2 ARYL 2H [1,2,4]TRIAZOLOISOQUINOLIN 3 ONE; 2 ARYL 2H [1,2,4]TRIAZOLOQUINOLIN 3 ONE; 2 PHENYL 2H [1,2,4]TRIAZOLO [3,4 A]ISOQUINOLIN 3 ONE; 2 PHENYL 2H [1,2,4]TRIAZOLO [4,3 A]QUINOLIN 3 ONE; ALPHA CHLOROFORMYLARYLHYDRAZINE HYDROCHLORIDE; ELECTROPHILE; HYDRAZINE DERIVATIVE; QUINOLINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; ISOMER; OXIDATION; PRIORITY JOURNAL; RING OPENING; SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 72449179546     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.11.095     Document Type: Article

References (15)

1. Silvestrini, B. U.S. Patent 3,381,009, 1968;
2. Marek G.J., McDougle C.J., Price H., and Seiden L.S. Psycopharmacology 109 (1992) 2-11
3. Caliendo G., Carlo R.D., Meli R., Perissutti E., Santagada V., Silipo C., and Vittoria A. Eur. J. Med. Chem. 28 (1993) 969-974
4. Betti L., Botta M., Corelli F., Floridi M., Fossa P., Giannaccini G., Manetti F., Strappaghetti G., and Corsano S. Bioorg. Med. Chem. Lett. 12 (2002) 437-440
5. Giannangeli M., Cazzolla N., Luparini M.R., Magnani M., Mabilia M., Picconi G., Tomaselli M., and Baiocchi L. J. Med. Chem. 42 (1999) 336-345
6. Palazzo, G. U.S. Patent 3,857,845, 1974.
7. Temple, D. L., Jr.; Lobeck, W. G., Jr. U.S. Patent 4,338,317, 1982.
8. Loscher W. Eur. J. Pharmacol. 342 (1998) 1-13
9. Jin H.-G., Sun X.-Y., Chai K.-Y., Piao H.-R., and Quan Z.-S. Bioorg. Med. Chem. Lett. 14 (2006) 6868-6873
10. Xie Z.S., Chai K.Y., Piao H.R., Kwak K.C., and Quan Z.S. Bioorg. Med. Chem. Lett. 15 (2005) 4803-4805
11. Cui L.-J., Xie Z.-F., Piao H.-R., Li G., Chai K.-Y., and Quan Z.-S. Biol. Pharm. Bull. 28 (2005) 1216-1220
12. Chiu C.-Y., Kuo C.-N., Kuo W.-F., and Yeh M.-Y. J. Chin. Chem. Soc. 49 (2002) 239-249
13. Bond lengths (Å) and angles (°) of 2-(p-Fluorophenyl)-2H-[1,2,4]triazolo-[4,3-a]quinolin-3-one (3c): F(1)-C(14), 1.364(2); C(14)-C(15), 1.366(2); C(14)-C(13), 1.364(2); C(15)-C(16), 1.382(2); C(11)-C(16), 1.388(2); N(1)-C(11), 1.424(2); C(11)-C(12), 1.388(2); C(12)-C(13), 1.383(2); N(1)-N(2), 1.388(2); N(1)-C(1), 1.376(2); O(1)-C(1), 1.219(2); N(3)-C(1), 1.395(2); N(3)-C(2), 1.378(2); N(2)-C(2), 1.300(2); N(3)-C(10), 1.413(2); C(2)-C(3), 1.433(2); C(5)-C(10), 1.404(2); C(9)-C(10), 1.391(2); C(8)-C(9), 1.379(2); C(7)-C(8), 1.388(2); C(6)-C(7), 1.371(2); C(5)-C(6), 1.401(2); C(4)-C(5), 1.441(2); C(3)-C(4), 1.339(2); C(3)-H(1), 0.95; C(4)-H(2), 0.95; C(6)-H(3), 0.95; C(7)-H(4), 0.95; C(8)-H(5), 0.95; C(9)-H(6), 0.95; C(12)-H(7), 0.95; C(13)-H(8), 0.95; C(15)-H(9), 0.95; C(16)-H(10), 0.95; N(2)-N(1)-C(1), 112.8(1); N(2)-N(1)-C(11), 119.1(1); C(1)-N(1)-C(11), 128.1(1); N(1)-N(2)-C(2), 104.2(1); C(1)-N(3)-C(2), 107.8(1); C(1)--N(3)-C(10), 129.1(1); C(2)-N(3)-C(10), 123.2(1); O(1)-C(1)-N(1), 129.2(1); O(1)-C(1)-N(3), 127.9(1); N(1)-C(1)-N(3), 102.8(1); N(2)-C(2)-N(3), 112.4(1); N(2)-C(2)-C(3), 128.1(1); N(3)-C(2)-C(3), 119.5(1); C(2)-C(3)-C(4), 118.5(1); C(3)-C(4)-C(5), 122.3(1); C(4)-C(5)-C(6), 121.8(1); C(4)-C(5)-C(10), 119.9(1); C(6)-C(5)-C(10), 118.3(1); C(5)-C(6)-C(7), 120.7(1); C(6)-C(7)-C(8), 120.1(2); C(7)-C(8)-C(9), 120.9(2); C(8)-C(9)-C(10), 119.1(1); N(3)-C(10)-C(5), 116.5(1); N(3)-C(10)-C(9), 122.6(1); C(5)-C(10)-C(9), 120.9(1); N(1)-C(11)-C(12), 118.7(1); N(1)-C(11)-C(16), 121.0(1); C(12)-C(11)-C(16), 120.2(1); C(11)-C(12)-C(13), 120.2(1); C(12)-C(13)-C(14), 118.4(2); F(1)-C(14)-C(13), 118.8(2); F(1)-C(14)-C(15), 118.5(2); C(13)-C(14)-C(15), 122.7(2); C(14)-C(15)-C(16), 119.3(2); C(11)-C(16)-C(15), 119.1(1); C(4)-C(3)-H(1), 120.8; C(2)-C(3)-H(1), 120.7; C(5)-C(4)-H(2), 118.8; C(3)-C(4)-H(2), 118.9; C(7)-C(6)-H(3), 119.7; C(5)-C(6)-H(3), 119.6; C(8)-C(7)-H(4), 119.9; C(6)-C(7)-H(4), 120.0; C(9)-C(8)-H(5), 119.6; C(7)-C(8)-H(5), 119.5; C(10)-C(9)-H(6), 120.4; C(8)-C(9)-H(6), 120.5; C(13)-C(12)-H(7), 119.9; C(11)-C(12)-H(7), 119.8; C(14)-C(13)-H(8), 120.8; C(12)-C(13)-H(8), 120.8; C(16)-C(15)-H(9), 120.3; C(14)-C(15)-H(9), 120.3; C(15)-C(16)-H(10), 120.5; C(11)-C(16)-H(10), 120.5.
14. Bond lengths (Å) and angles (°) of 2-(p-Chlorophenyl)-2H-[1,2,4]triazolo-[3,4-a]-isoquinolin-3-one (4d): C(1)-C(2), 1.367(5); C(1)-C(6), 1.388(5); C(1)-Cl, 1.739(3); C(2)-C(3), 1.376(5); C(3)-C(4), 1.394(5); C(4)-C(5), 1.380(5); C(4)-N(1), 1.413(4); C(5)-C(6), 1.376(5); C(7)-N(1), 1.372(4); C(7)-N(2), 1.390(4); C(7)-O(7), 1.217(4); C(8)-C(9),1.449(4); C(8)-N(2), 1.371(4); C(8)-N(3), 1.299(4); C(9)-C(10), 1.407(4); C(9)-C(16), 1.389(5); C(10)-C(11), 1.453(5); C(10)-C(13), 1.409(5); C(11)-C(12), 1.332(6); C(12)-N(2), 1.392(4); C(13)-C(14), 1.369(7); C(14)-C(15), 1.384(6); C(15)-C(16), 1.382(5); N(1)-N(3), 1.398(3); C(2)-C(1)-C(6), 121.0(3); C(2)-C(1)-Cl, 119.2(3); C(6)-C(1)-Cl, 119.9(3); C(1)-C(2)-C(3), 120.0(3); C(2)-C(3)-C(4), 119.9(3); C(3)-C(4)-C(5), 119.3(3); C(3)-C(4)-N(1), 120.4(3); C(4)-C(5)-C(6), 120.9(3); C(1)-C(6)-C(5), 118.9(3); N(1)-C(7)-N(2), 102.5(3); N(1)-C(7)-O(7), 130.6(3); N(2)-C(7)-O(7), 126.9(3); C(9)-C(8)-N(2), 118.7(3); C(9)-C(8)-N(3), 129.2(3); N(2)-C(8)-N(3), 112.1(3); C(8)-C(9)-C(10), 117.0(3); C(8)-C(9)-C(16), 122.1(3); C(10)-C(9)-C(16), 120.9(3); C(9)-C(10)-C(11), 120.6(3); C(9)-C(10)-C(13), 117.8(3); C(11)-C(10)-C(13), 121.6(3); C(10)-C(11)-C(12), 120.6(3); C(11)-C(12)-N(2), 119.0(4); C(10)-C(13)-C(14), 120.6(4); C(14)-C(15)-C(16), 119.9(4); C(9)-C(16)-C(15), 119.9(3); C(4)-N(1)-C(7), 127.5(3); C(4)-N(1)-N(3), 119.6(2); C(7)-N(1)-N(3), 112.9(2); C(7)-N(2)-C(8), 108.6(2); C(7)-N(2)-C(12), 127.3(3); C(8)-N(2)-C(12), 124.0(3); C(8)-N(3)-N(1), 103.9(2).
15. Ullah E., Rotzoll S., Schmidt A., Michalik D., and Langer P. Tetrahedron Lett. 46 (2005) 8997-8999