A structurally diverse heterocyclic library: A benzothiazepine-fused β-lactam library derived from reaction of 2,3-dihydro-1,5-benzothiazepines and acyl chlorides: Synthesis and stereochemistry

Molecular Diversity

Volumn 9, Issue 1-3, 2005, Pages 45-49

  Xu, Jiaxi ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

lactam; Acyl chloride; Benzothiazepine; Heterocyclic library; Parallel synthesis; Solution phase synthesis; Stereochemistry

Indexed keywords

1H AZETO[2,1 D][1,5]BENZOTHIAZEPIN 1 ONE; ACETIC ACID DERIVATIVE; BENZOTHIAZEPINE DERIVATIVE; BETA LACTAM DERIVATIVE; CHLORINE DERIVATIVE; CHLOROACETYL CHLORIDE; DICHLOROACETYL CHLORIDE; HETEROCYCLIC COMPOUND; PHENOXYACETYL CHLORIDE; PHTHALIMIDOACETYL CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; BIODIVERSITY; DRUG SYNTHESIS; PARALLEL DESIGN; PHASE TRANSITION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

BENZOTHIADIAZINES; BETA-LACTAMS; CHLORIDES; CHROMATOGRAPHY, THIN LAYER; HETEROCYCLIC COMPOUNDS, 2-RING; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 15544384476     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-005-1306-x     Document Type: Article

References (22)

1. Durkheimer, W., Blumbach, J., Lattrell, K. and Scheunemann, K.H., Recent developments in the field of β-lactam antibiotics, Angew. Chem. Int. Ed., 97 (1985) 180-202.
2. Morin, R.B. and Gorman, M., Chemistry and Biology of β-Lactam Antibiotics, vols. 1-3, Academic Press, 1982.
3. Southgate, R. and Elson, S., In The Chemistry of Organic Natural Products, vol. 47 (Eds. Herz, W., Grisebach, H., Kirby, G. W., Tamm, Ch.), Springer-Verlag, Wien, 1985.
4. van der Steen, F.H. and van Koten, G., Syntheses of 3-amino-2- azetidinones: A literature survey, Tetrahedron, 47 (1991) 7503-7524.
5. Palomo, C., Aizpurua, J.M., Ganboa, I. and Oiarbide, M., Asymmetric synthesis of β-lactams by Staudinger ketene-imine cycloaddition reaction, Eur. J. Org. Chem., (1999) 3223-3235.
6. Bose, A.K., Manhas, M.S., Chib, J.S., Chawla, H.P.S. and Dayal, B., Studies on β-lactams. XXXVI. Monocyclic cis β-lactams via penams and cephams, J. Org. Chem., 39 (1974) 2877-2884.
7. Firestone, R.A., Maciejewicz, N.S. and Christensen, B.G., Total synthesis of β-lactam antibiotics. VI. 3-Arylcephalosporin, J. Org. Chem., 39 (1974) 3384-3387.
8. Hegedus, L.S., Imwinkelried, R., Alarid-Sargent, M., Dvorak, D. and Satoh, Y., Synthesis of optically active β-lactams by the photolytic reaction of imines with optically active chromium carbene complexes, J. Am. Chem. Soc., 112 (1990) 1109-1117.
9. Xu, J.X. and Tin, S., Thermal cycloaddition reaction of symmetrical and unsymmetrical α-diazo-β-diketones with 4-aryl-2-methyl-2,3-dihydro-1, 5-benzothia/diazepines, Heteroat. Chem., 10 (1999) 35-40.
10. Xu, J.X. and Jin, S., New heterocyclic system synthesis IV: 4a,5,6,12-Tetrahydro-1H-1,3-oxazino[3,2-d][1,5]benzothiazepine-1-one, Chin. Chem. Lett., 3 (1992) 181-182.
11. Xu, J.X. and Chen, L.B., Synthesis of oxazirino[2,3-a][1,5]benzodiaze pines by oxidation of 1H-1,5-benzodiazepines with m-chloroper benzoic acid (MCPBA), Heteroat. Chem., 11 (2000) 158-162.
12. Xu, J.X., Wu, H.T. and Jin, S., Cycloaddition reaction of benzoheteroazepine II: Reactions and conformations of cycloadducts on 1,5-benzothiazepines and 1,5-benzodiazepines with nitrile imine and nitrile oxides, Chin. J. Chem., 17 (1999) 84-91.
13. Xu, J.X., Jin, S. and Xing, Q.Y., Cycloaddition reaction of benzoheteroazepine: Synthesis of 4a,5,6,12-tetrahydro-1H-1,3-oxazino[3,2-d][1,5] benzothiazepin-1-ones and 1H,7H-1,3-oxazino[3,2-d][1,5] benzodiazepin-1-ones. Phosphorus Sulfur Silicon Relat. Elem., 141 (1998) 57-70.
14. Xu, J.X., Zuo, G. and Chan, W.-L., Reaction of 2,3-dihydro-1H-1,5- benzodiazepines and chloroacetyl chlorides: Synthesis of 2a,3,4, 5-tetrahydro-azeto[1,2-a][1,5]benzodiazepin-1(2H)-ones, Heteroat. Chem., 12 (2001) 636-640.
15. Szollosy, A., Kotovych, G., Toth, C. and Levai, A., The synthesis and the nuclear magnetic resonance study of β-lactam derivatives of 1,5-benzothiazepines, Can. J. Chem., 66 (1988) 279-282.
16. Pippich, S., Bartsch, H. and Erker, T., Studies on the chemistry of O,N-and S,N-containing heterocycles. 16. Investigations on the synthesis of new tricyclic β-lactams via [2+2] cycloaddition reaction, J. Heterocycl. Chem., 34 (1997) 823-828.
17. Martinez, R., Hernandez, P.E. and Angeles, E., Heterocyclic variants of 1,5-benzodiazepine system. VII. Synthesis of substituted 2a-phenyl-4- methylsulfonyl-2-methoxy-1,2,2a,3-tetrahydroazeto[1,2-a][1,5] benzodiazepin-1-ones, J. Heterocycl. Chem., 33 (1996) 271-274.
18. 2-phenyl)-3H-1,5-benzodiazepines, J. Heterocycl. Chem., 26 (1989) 119-124.
19. Xing, Q.Y., Wang, H.Z., Zhou, X., Jin, S., Li, Y.M. and Chan, A.S.C., A study of the reaction between 2,4-disubstituted 2,3-dihydro-1,5-benzothiazepines and ketenes generated in situ from chloro- and dichloroacetyl chlorides, J. Hetercycl. Chem., 38 (2001) 561-567.
20. Lu, Y.C., Jin, S. and Xing Q. Y., Theoretical conformational analysis of 1,5-benzodiazepines and benzothiazepines, Theochem. J. Mol. Struct., 44 (1988) 253-267.
21. Xu, J.X., Zuo, G., Zhang, Q.H. and Chan, W.L., Stereospecific synthesis of 2-phthalimido-2a,3,4,5-tetrahedro-1H-azeto[2,1-d][1,5]benzothiazepin-1-ones, Heteroat. Chem., 13 (2002) 165-168.
22. Huang, X. and Xu, J.X., Stereospecific synthesis of azeto[2,1-d][1,5] benzothiazepin/diazepine-1-ones, Heteroat. Chem., 14 (2003) 654-659.