Efficient tetrahydrosalen synthesis from Mannich-type bases

Synthetic Communications

Volumn 34, Issue 13, 2004, Pages 2479-2485

  Rivera, Augusto ^a   Quevedo, Rodolfo ^a   Navarro, Miguel A ^a   Maldonado, Mauricio ^a  

^a UNIVERSIDAD NACIONAL DE COLOMBIA   (Colombia)

Author keywords

Ethylenediamine; Formaldehyde; Mannich type bases; Tetrahydrosalen

Indexed keywords

ALDEHYDE DERIVATIVE; ETHYLENEDIAMINE DERIVATIVE; HYDROCHLORIC ACID; IMIDAZOLIDINE DERIVATIVE; MANNICH BASE; TETRAHYDROSALEN; UNCLASSIFIED DRUG;

ARTICLE; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 3543071770     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120039502     Document Type: Article

References (11)

1. Tshuva, E.Y.; Gendeziuk, N.; Kol, M. Single-step synthesis of salens and substituted salans by Mannich condensation. Tetrahedron Lett. 2001, 42, 6405-6408.
2. Davis, T.J.; Balsells, J.; Carroll, P.J.; Walsh, P.J. Optimization of asymmetric catalysts using achiral ligands: metal geometry-induced ligand asymmetry. Org. Lett. 2001, 3 (14), 2161.
3. Tshuva, E.Y.; Goldberg, I.; Kol, M. Isospecific living polymerization of 1-hexene by a readily available nonmetallocene C2-symmetrical zirconium catalyst. J. Am. Chem. Soc. 2000, 122, 10706-10707.
4. Balsells, J.; Walsh, P.J. The use of achiral ligands to convey asymmetry: chiral environment amplification. J. Am. Chem. Soc. 2000, 122, 1802-1803.
5. 2-symetric titaniun complexes: a structure and diastereoselectivity study. Inorg. Chem. 2001, 40, 5568-5574.
6. Subramaniam, P.; Spence, J.T.; Ortega, R.; Enemark, J.H. Molybdenum(VI)-dioxo complexes with sterically bulky ligands. Inorg. Chem. 1984, 23, 2564-2567.
7. Hinshaw, C.J.; Peng, G.; Singh, R.; Spence, J.T.; Enemark, J.H.; Bruck, M.; Kristofzski, J.; Merbs, S.L.; Ortega, R.B.; Wexler, P.A. Molybdenum (VI)-dioxo complexes with linear and tripodal tetradentate ligands: models for the molybdenum(VI/V) centers of the molybdenum hydroxylases and related enzymes. 1. Syntheses and structures. Inorg. Chem. 1989, 28, 4483.
8. Rivera, A.; Léon, J.; Rivera, J.; Parra, E.; Purmova, J.; Burgueño-Tapia, E.; Joseph-Nathan, P. Synthesis of 2t-substituted-lr,3c- bis(2′hydroxy-5′-substituted-benzyl)-imidazolidines by reaction of 1,3-bis(2′-hydroxy-5′-subsbtuted-benzyl)-imidazolidines with aromatic aldehydes. Synth. Commun. 2000, 30 (11), 2029-2040.
9. Rivera, A.; Gallo, G.L.; Gayón, M.E.; Joseph-Nathan, P. A novel mannich type reaction using aminals in alkaline medium. Synth. Commun. 1993, 23 (20), 2921-2930.
10. Simkins, R.J.; Wright, G.F. Nitrolysis of 1,3-6,8-diendomethylene-1,3,6, 8-tetrazacyclodecane. J. Am. Chem. Soc. 1955, 77, 3157-3158.
11. Lee, E.; Kim, S.; Jung, B.H.; Ahn, W.; Kim, G. New enantioselective chiralimidazolidine ligands for Pd-catalyzed asymmetric allylic alkylation. Tetrahedron Lett. 2003, 44, 1971-1974.