A novel and efficient iodine(III)-mediated access to 1,4-benzodiazepin-2-ones

Tetrahedron Letters

Volumn 43, Issue 46, 2002, Pages 8273-8275

  Herrero, M Teresa ^a   Tellitu, Imanol ^a   Domínguez, Esther ^a   Moreno, Isabel ^a   SanMartín, Raúl ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; ALANINE DERIVATIVE; AMIDE; BENZODIAZEPINE DERIVATIVE; FLUOROACETIC ACID; GLYCINE DERIVATIVE; IODINE; PHENYL GROUP;

ACYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; DRUG DESIGN; ENANTIOMER; HYDROLYSIS; RACEMIZATION;

EID: 0037064493     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02019-1     Document Type: Article

References (29)

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12. Some review articles on the synthesis of 1,4-benzodiazepines: (a) Joshi, B.; Chauhan, M. Ind. J. Heterocycl. Chem. 1996, 6, 157-164; (b) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 431-543; (c) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 545-629; (d) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 631-848; (e) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 849-946; (f) Bunin, B. A.; Plunkett, M. J. Methods Enzymol. 1996, 267, 448-465.
13. Some review articles on the synthesis of 1,4-benzodiazepines: (a) Joshi, B.; Chauhan, M. Ind. J. Heterocycl. Chem. 1996, 6, 157-164; (b) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 431-543; (c) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 545-629; (d) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 631-848; (e) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 849-946; (f) Bunin, B. A.; Plunkett, M. J. Methods Enzymol. 1996, 267, 448-465.
14. Some review articles on the synthesis of 1,4-benzodiazepines: (a) Joshi, B.; Chauhan, M. Ind. J. Heterocycl. Chem. 1996, 6, 157-164; (b) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 431-543; (c) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 545-629; (d) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 631-848; (e) Walser, A.; Fryer, R. I. Chem. Heterocycl. Compd. 1991, 50, 849-946; (f) Bunin, B. A.; Plunkett, M. J. Methods Enzymol. 1996, 267, 448-465.
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21. (a) For a recent contribution of our group referred to the synthesis of quinolinones employing this strategy, see: Herrero M.T., Tellitu I., Hernández S., Domínguez E., Moreno I., SanMartín R. ARKIVOC. v:2002;31-37.
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25. This substrate was prepared following standard procedures by reductive amination of benzaldehyde with (S)-alanine methyl ester.
26. 2O was employed to avoid, as detected under other conditions, racemization at this stage.
27. N,N-Dibenzyl substituted precursors of type 4 were also prepared but the corresponding final cyclization step proceeded with limited success (20% yield for the corresponding N-benzyl-N-methoxy-3-methyl-1,4-benzodiazepin-2-one). This and other ancillary studies that facilitated the synthesis' achievement will be reported elsewhere.
28. 4 264.1115, found 264.1110.
29. iPrOH (98/2), 0.7 mL/min.