A facile approach for new dibenzo [b,f][1,5] diazocinones

Synthetic Communications

Volumn 35, Issue 11, 2005, Pages 1493-1500

  Pessoa Mahana, Hernán ^a   Martínez Aránguiz, Karen G ^a   Araya Maturana, Ramiro ^a   Pessoa Mahana, C David ^b  

^a UNIVERSITY OF CHILE   (Chile)

^b PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

Dibenzodiazocinones; Nitroaldehydes; Tr ger's base

Indexed keywords

7,10 DIMETHOXY DIBENZO[B,F][1,5] DIAZOCINE 6 (5H) ONE; DIBENZO[B,F][1,5] DIAZOCINE 6 (5H) ONE; DIBENZODIOXAZOCINE DERIVATIVE; N(2 FORMYLPHENYL) 2 NITROBENZAMINE; N(2 FORMYLPHENYL) 3,6 DIMETHOXY 2 NITROBENZAMINE; NITROBENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; REDUCTION; SYNTHESIS;

EID: 20844441786     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200057990     Document Type: Article

References (13)

1. 2-symmetric and asymmetric 2,8-disubstituted analogues of Tröger's base via efficient bromine-lithium exchanges of 2,8-dibromo-6H,12H-5,11-methanodibenzo [b,f] [1,5] diazocine. J. Org. Chem. 2002, 67, 6008-6014.
2. Jensen, J.; Wärnmark, K. Synthesis of halogen substituted analogues of Tröger's base. Synthesis 2001, 12, 1873-1877.
3. Hansson, A.; Jensen, J.; Wendt, O. F.; Warnmark, K. Synthesis of dihalo-substituted analogues of Tröger's base from ortho and meta-substituted anilines. Eur. J. Org. Chem 2003, 16, 3179-3188.
4. Demeunynck, M.; Tatiboüet, A. Recent developments in Tröger's base chemistry. In Progress in Heterocyclic Chemistry; Gribble, G. W., Gilchrist, T. L. eds. Pergamon: Oxford, U.K., 1999; Vol. 11, pp. 1-20.
5. Tatibouet, A.; Demeunynck, M.; Andraud, C.; Collet, A.; Lhomme, J. Synthesis and study of an acridine substituted Tröger's base: Preferential binding of the (-) isomer to B-DNA. Chem. Commun. 1999, 2, 161-162.
6. Harmata, M.; Kahraman, M. Congeners of Tröger's base as chiral ligands. Tetrahedron: Asymmetry 2000, 11, 2875-2879.
7. Kamal, A.; Venkata Ramana, K.; Antaki, H. B.; Venkata Ramana, A. Mild and efficient reduction of azides to amines: Synthesis of fused [2,1-b] quinazolines. Tetrahedron Lett. 2002, 43, 6861-6863.
8. Miyahara, I.; Izumi, K.; Ibrahim, A. A.; Inazu, T. Novel C-2 chiral diamine ligands derived from cyclic Tröger bases. Tetrahedron Lett. 1999, 40, 1705-1708.
9. Eguchi, S.; Matushita, Y.; Takeuchi, H. Novel synthetic route to benzopolyazamacrocycles. Synthesis of 16-membered tetrabenzotetraazamacrocycles via bisquinazolinone annelation and reductive ring enlargement. J. Org. Chem. 1992, 57, 6975-6979.
10. Hassner, A.; Sun, B.; Gellermann, G.; Meir, S. Dilactams. Synthesis of nonsymmetrical dibenzodiazocinediones. Tetrahedron Lett. 2004, 45, 1377-1379.
11. Wakankar, D. M.; Hosangadi, B. D. Studies in large ring compounds: Part VI. Synthesis of 5,11-disubstituted dibenzo [b,f] [1,5] diazocine-6,12 (5H, 11H)-diones. Indian J. Chem. 1984, 23, 136-139.
12. Valderrama, J. A.; Pessoa-Mahana, H.; Sarrás, G.; Tapia, R. Access to quinazolines from 2-nitrobenzaldehyde and arylamines. Heterocycles 1999, 51, 2193-2201.
13. Pessoa-Mahana, H.; Pessoa-Mahana, C. D.; Salazar, R.; Saez, E.; Valderrama, J. A.; Araya-Maturana, R. Solvent free synthesis of 6-arylbenzimidazo [1,2-c]quinazolines under microwave irradiation. Synthesis 2004, 3, 436-440.