Substitution of the benzotriazolyl group in N-(α -amidoalkyl)benzotriazoles and N-(α-sulfonamidoalkyl)benzotriazoles with allylsamarium bromide

Synthetic Communications

Volumn 33, Issue 20, 2003, Pages 3575-3581

  Wang, Xiaoxia ^a   Li, Jian ^a   Zhang, Yongmin ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allylsamarium bromide; Homoallylamide; Homoallylsulfonamide; N ( Sulfonamidoalkyl)benzotriazoles; N ( Amidoalkyl)benzotriazoles

Indexed keywords

BENZOTRIAZOLE DERIVATIVE; BENZOTRIAZOLYL DERIVATIVE; SAMARIUM; SAMARIUM BROMIDE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELIMINATION REACTION; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0141865666     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120024744     Document Type: Article

References (14)

1. (a) Katritzky, A.R.; Rachwal, S.; Hitchings, G.J. A novel synthetic auxiliary. Tetrahedron 1991, 47, 2683;
2. (b) Katritzky, A.R.; Yang, Z.; Cundy, D.J. Benzotriazole-stabilized carbanions: generation, reactivity and synthetic utility. Aldrichimica Acta 1994, 27, 31;
3. (c) Katritzky, A.R.; Lan, X. Benzotriazole-mediated arylarylation and heteroarylalkylation. Chem. Soc. Rev. 1994, 363;
4. (d) Katritzky, A.R.; Lan, X.; Fan, W.Q. Benzotriazole as a synthetic auxiliary: benzotriaxolylalkylation and benzotriazole-mediated heteroalkylation. Synthesis 1994, 445;
5. (e) Katritzky, A.R.; Lan, X.; Yang, J.Z.; Denisko, O.V. Properties and synthetic utility of N-substituted benzotriazoles. Chem. Rev. 1998, 98, 409.
6. Yu, M.X.; Zhang, Y.M.; Guo, H.Y. The synthesis of homoallylaminised by the addition of oransamarium reagent to nitriles. Synth. Commun. 1997, 27, 1495.
7. Fan, X.S.; Zhang, Y.M. Preparation of dihomoallylic secondary amines through samarium mediated allylation of oximes. Tetrahedron Lett. 2002, 43, 5475.
8. (a) Li, Z.F.; Zhang, Y.M. Direct construction of quaternary carbon center utilizing an organosamarium reagent. Tetrahedron Lett. 2001, 42, 8507;
9. (b) Li, Z.F.; Zhang, Y.M. Direct construction of quaternary carbon center utilizing an allylsamarium bromide reagent. Tetrahedron 2002, 58, 5301.
10. Wang, J.; Zhou, J.; Zhang, Y. Facile preparation of homoallylamines via reaction of N-aminoalkylbenzotriazoles with allylsamarium bromide. Synth. Commun. 1996, 26, 3395.
11. Katritzky, A.R.; Drewniak, M. The chemistry of benzotriazole. Part 8. A novel two-step procedure for the N-alkylation of amides. J. Chem. Soc. Perkin Trans. 1 1988, 2339.
12. Katritzky, A.R.; Oniciu, D.D.; Ghiviriga, I. Benzotriazole-assisted synthesis of N-(α-cyanoalkyl)sulfonamides. Synth. Commun. 1997, 27, 907.
13. Liu, Y.K.; Zhang, Y.M. J. Chem. Res. (S) in press.
14. Lu, W.S.; Chan, T.H. Organometallic reactions in aqueous media. Indium- and zinc-mediated allylation of sulfonimines. J. Org. Chem. 2000, 65, 8589.