Domino-reaction of oxal(imidoyl)chlorides with 3-aminoisoxazoles: Regio- and stereoselective synthesis of 1,4-dihydro-imidazo[4,5-b]quinoxalines

Synlett

Volumn , Issue 4, 1999, Pages 468-470

  Wuckelt, Jörg ^a   Döring, Manfred ^a   Langer, Peter ^b   Beckert, Rainer ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Ambident nucleophiles; Domino reactions; N heterocycles; Oxalic acid dielectrophiles; Regioselective cyclizations

Indexed keywords

1,4 DIHYDROIMIDAZO[4,5 B]QUINOXALINE; CLOFAZIMINE; OXALIC ACID DERIVATIVE; RIBOFLAVIN; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0344507368     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2636     Document Type: Article

References (14)

1. Reviews: (a) Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137; Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
2. Reviews: (a) Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137; Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
3. (b) de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
4. (b) de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
5. (a) Beckert, R.; Mayer, R. Wiss. Z. Techn. Univers. Dresden 1987, 2, 36.
6. (b) Iida, T.; Itaya, T. Tetrahedron 1993, 49, 10511.
7. (a) Langer, P.; Döring, M.; Görls, H.; Beckert, R. Liebigs Ann/Recueil 1997, 2553.
8. (b) Langer, P.; Döring, M. Synlett 1998, 396.
9. Lindauer, D; Beckert, R.; Billert, T.; Döring, M.; Görls, H. J. Prakt. Chem., 1995, 337, 143.
10. Zhou, R.; Skibo, E. B. J. Med. Chem. 1996, 39, 4321.
11. 3), 88.8, 116.2, 126.8, 128.0, 130.7, 131.4, 133.2, 134.6, 137.9, 141.0, 149.2, 150.1, 206.0. All new compounds gave satisfactory spectroscopic and analytical and/ or high resolution mass data.
12. For the cleavage of the isoxazole N-O bond by hydrogenation, see: (a) Katritzky, A. J. Chem. Soc. 1957, 191.
13. (b) Büchi, G.; Vederas, J. C.; J. Am. Chem. Soc. 1972, 94, 9128.
14. (c) Ruccia, M.; Vivona, N.; Spinelli, D. Adv. Heterocycl. Chem. 1981, 29, 141.