Efficient synthesis of N-cyano α and β-amino esters

Synthetic Communications

Volumn 38, Issue 9, 2008, Pages 1375-1380

  Sathe, Manisha ^a   Karade, Hitendra N ^a   Kaushik, M P ^a  

^a DEFENCE RESEARCH AND DEVELOPMENT ESTABLISHMENT   (India)

Author keywords

Amino ester; Cyanogen bromide; N cyano amino ester

Indexed keywords

BETA AMINO ACID; BROMIDE; ESTER;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; CYANATION; SYNTHESIS;

EID: 42149166797     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801914145     Document Type: Article

References (15)

1. Fulop, F. The chemistry of 2-aminocycloalkanecarboxilic acids. Chem. Rev. 2001, 101, 2181.
2. Gyonfalvi, S.; Szakonyi, Z.; Fulop, F. Synthesis and transformation of novel cyclic β-amino acid derivatives from (+)-careen. Tetrahedron: Asymmetry 2003, 14, 3965.
3. (a) Katritzky, R.; Kirichenko, N.; Rogovoy, B. V. Synthesis of mono- and N,N-disubstituted ureas. Arkivoc 2003, 8, 8;
4. (b) Koketsu, M.; Fukuta, Y.; Ishihara, H. An alternative route for the construction of carbosilane dendrimers uniformly functionalized with lactose or sialyllactose moieties. Tetrahedron Lett. 2001, 42, 3327;
5. (c) Domount, F.; Sultana, A.; Waterhouse, R. N. Synthesis and in vitro evaluation of N,N′-diphenyl and N-naphthyl-N′- phenylguanidines as N-methyl-D-aspartate receptor ion-channel ligands. Bioorg. Med. Chem. Lett. 2002, 12, 1583;
6. (d) Donetti, A.; Bellora, E. J. A mild and effective two-step conversion of disubstituted cyanamides to secondary amines. J. Org. Chem. 1972, 37, 3352.
7. Park, J. S.; Lee, H. S.; Lai, J. R.; Kim, B. M.; Gellman, S. H. Accommodation of α-substituted residues in the β-peptide 12-helix: Expanding the range of substitution patterns available to a foldamer scaffold. J. Am. Chem. Soc. 2003, 125, 8539.
8. (a) Jonczyk, A.; Ochal, Z.; Makosazm, M. Reactions of organic anions, LXXXV. Catalytic two-phase alkylation of cyanamide. Synthesis 1978, 882;
9. (b) Snider, B. B.; O'Hare, S. M. Synthesis of the hindered N,N,N′-trisubstituted guanidine moiety of martinelline and martinellic acid. Tetrahedron Lett. 2001, 42, 2455;
10. (c) Bialey, D.; deGrazia, C. G.; Lape, H. E.; Frering, R.; Fort, D.; Skulan, T. Hydroxyguanidines: A new class of antihypertensive agents. J. Med. Chem. 1973, 16, 151.
11. Barrett, D. G.; Deaton, D. N.; Hassell, A. M.; McFadyen, B. R.; Miller, L. R.; Payne, J. A.; Shewchuk, L. M.; Willard, D. H.; Wright, L. L. Acyclic cyanamide-based inhibitors of cathepsin K. Bioorg. Med. Chem. Lett. 2005, 15, 3039.
12. Herrera, A.; Martinez-Alvarez, R.; Ramiro, P.; Chioua, M.; Chioua, R. A practical and easy synthesis of 2,4,6-trisubstituted-s-triazines. Synthesis 2004, 503.
13. Kumar, V. Cyanogen bromide (CNBr). Synlett 2005, 1638.
14. (a) Sathe, M.; Ghorpade, R.; Kaushik, M. P. Highly efficient methanolysis of bicyclic β-lactams to β-amino ester using silica chloride. Chem. Lett. 2006, 35, 1004;
15. (b) Parsons, P. J.; Camp, N. P.; Underwood, J. M.; Harvey, M. D. Tandem reactions of anions: A short and efficient route to ±anatoxin-a. Tetrahedron 1996, 52, 11637.