Synthesis of Monocyclic β‐Lactams via Cyclodehydration of β‐Amino Acids Using POCl₃

References

• Macdonald , S. J.F. , Inglis , G. G.A. , Bentley , D. and Dowle , M. D. 2002 . Synthesis of templates derived from pyrrolidine trans lactams as potential serine protease inhibitors . Tetrahedron Lett. , 43 ( 29 ) : 5057 – 5060 .
   Google Scholar
• Wilmouth , R. C. , Kassamally , S. , Westwood , N. J. , Sheppard , R. J. , Claridge , T. D.W. , Aplin , R. T. , Wright , P. A. , Pritchard , G. J. and Schofield , C. J. 1999 . Mechanistic insights into the inhibition of serine proteases by monocyclic lactams . Biochemistry , 38 : 7989 – 7998 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Yoakim , C. , Ogilvie , W. W. , Cameron , D. R. , Chabot , C. , Guse , I. , Hache , B. , Naud , J. , O'Meara , J. A. , Plante , R. and Deziel , R. 1998 . β‐Lactam derivatives as inhibitors of human cytomegalovirus protease . J. Med. Chem. , 41 : 2882 – 2891 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMedGoogle Scholar
• Talbot , M. D. and Butler , K. D. 1992 . Viral hemorrhagic fever . Drug News Prospect , 3 : 357 – 363 . [CSA]
   Google Scholar
• Qian , X. , Zheng , B. , Burke , B. , Saindane , M. T. and Kronental , D. R. 2002 . A stereoselective synthesis of BMS‐262084, an azetidinone based tryptase inhibitor . J. Org. Chem. , 67 : 3595 – 3600 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Smith , D. M. , Kazi , A. , Smith , L. , Long , T. E. , Heldreth , B. , Turos , E. and Dou , Q. P. 2002 . A novel β‐lactam antibiotic activates tumor cell apoptotic program by inducing DNA damage . Molecular Pharmacol. , 61 ( 6 ) : 1348 – 1358 . [CROSSREF] [CSA]
   PubMedGoogle Scholar
• Holley , R. W. and Holley , A. D. 1949 . Synthesis and reactivity of some 1‐alkyl‐2‐azetidinones (N‐alkyl‐β‐lactams) . J. Am. Chem. Soc. , 71 : 2124
   Google Scholar
• Dobrev , A. and Ivanov , C. 1971 . Synthesis and reactions of N‐substituted 3‐aminopropionic acids VI. Preparation of 2‐aryl‐3‐benzamino‐3,3‐diphenyl propionic acids and their transformation into N‐benzoyl azetidin‐2‐ones . Chem. Ber. , 104 : 981 [PUBMED] [INFOTRIEVE]
   PubMedGoogle Scholar
• Kampe , K. D. 1970 . Enantiomeric 4‐methyl‐2‐azetidinones . Chem. Abs. , 73 : p45313
   Google Scholar
• Fontanella , L. and Testa , E. 1959 . Substances acting on the central nervous system IX. 3,3‐Disubstituted 2‐azetidinone . Annalen , 622 : 117
   Google Scholar
• Blicke , F. F. and Gould , W. A. 1958 . Synthesis of 2‐azetidiones (β‐lactams) . J. Org. Chem. , 23 : 1102
   Google Scholar
• Testa , E. and Fontanella , L. 1962 . Azetidinones . Chem. Abs. , 56 : p1429f
   Google Scholar
• Woodward , R. B. 1971 . Azetidine compounds . Chem. Abs. , 75 : p140833
   Google Scholar
• Woo , K. C. , Young , C. B. and Sunggak , K. 1990 . New methods for β‐lactam formation from β‐amino acids with organophosphorous compounds . Tetrahedron Lett. , 31 : 2905 [CROSSREF]
   Google Scholar
• Palomo , C. , Aizpurua , J. M. , Urchegui , R. and Iturburu , M. 1991 . A convenient method for β‐lactam formation from β‐amino acids using phenyl phosphorodichloridate reagent . J. Org. Chem. , 56 : 2244
   Google Scholar
• Loewe , M. F. , Cvetovich , R. J. and Hazen , G. G. 1991 . An efficient β‐amino acid cyclodehydration using methanesulfonyl chloride to thienamycin intermediate 3‐(1‐hydroxyethyl)‐4‐(methoxycarbonylmethyl)‐azetidin‐2‐one . Tetrahedron Lett. , 32 : 2299 [CROSSREF]
   Google Scholar
• Toshiyuki , M. , Toyohiko , K. and Takashi , M. 1995 . A convenient preparative method for β‐lactams from β‐amino acids using sulphenamide/triphenylphosphine . Tetrahedron Lett. , 36 : 3703 [CROSSREF]
   Google Scholar
• Lee , Y. H. , Kim , H. C. and Lee , C. 1996 . Phosphorodimorpholidic halides as a new condensing agent for the formation of β‐lactams from β‐amino acids . Bull. Korean Chem. Soc. , 17 ( 7 ) : 656 – 657 .
   Google Scholar
• Lee , Y. H. , Lee , C. and Choi , W. S. 1996 . A new method for β‐lactam formation from β‐amino acids using N,N‐(diethoxyphosphinyl)benzo‐1,2,5‐thiazolidine 1,1‐dioxide . Bull. Korean Chem. Soc. , 17 ( 3 ) : 290 – 291 .
   Google Scholar
• Nagao , Y. , Kumagai , T. , Tamai , S. , Matsunaga , H. , Abe , T. and Inoue , Y. 1996 . A facile synthesis of β‐lactams by the cyclization of β‐amino acids exploiting 3,3′‐(phenylphosphoryl)‐bis(1,3‐thiazolidine‐2‐thione) . Heterocycles , 42 ( 2 ) : 849 – 859 .
   Google Scholar
• Sharma , S. D. and Kanwar , S. 1998 . Phosphorous oxychloride (POCl3): a key molecule in organic synthesis . Ind. J. Chem. , 37B : 965 – 978 .
   Google Scholar
• Sharma , S. D. , Gupta , P. K. and Bindra , J. 1980 . Conversion of some monocyclic β‐lactams into novel di‐β‐lactams . Tetrahedron Lett. , 21 : 3295 – 3298 . [CROSSREF]
   Google Scholar
• Sharma , S. D. , Singh , G. and Gupta , P. K. 1978 . Synthesis of azetidinones (β‐lactams) through phosphorous oxychloride method . Ind. J. Chem. , 16B : 74
   Google Scholar
• Zilkha , A. and Rivlin , J. 1958 . Synthesis of DL‐β‐aminobutyric acid and its N‐alkyl derivatives . J. Org. Chem. , 23 : 94 – 96 .
   Google Scholar
• Johnson , T. B. and Lovak , J. E. 1936 . Researches on pyrimidines CXLIX. The synthesis of aryl substituted dihydrouracils and their conversion to uracil derivatives . J. Am. Chem. Soc. , 58 : 299
   Google Scholar
• Holley , R. W. and Holley , A. D. 1949 . Synthesis and reactivity of some 1‐alkyl‐2‐azetidinones (N‐alkyl‐β‐lactams) . J. Am. Chem. Soc. , 71 : 2124
   Google Scholar
• Greenstein , J. P. 1961 . Chemistry of Amino Acids Vol. 2 , 1006 New York : John Wiley .
   Google Scholar
• Huang , H. , Iwasawa , N. and Mukaiyama , T. 1984 . A convenient method for the construction of β‐lactam compounds from β‐amino acids using 2‐chloro‐1‐methyl pyridinium iodide as condensing agent . Chem. Lett. , 8 : 1465
   Google Scholar
• Kim , S. , Lee , P. H. and Lee , T. A. 1988 . New methods for β‐lactam formation from β‐amino acids using triphenyl phosphine/carbon tetrachloride and triphenylphosphine/N‐bromosuccinimide . Synth. Commun. , 18 : 247
   Web of Science ®Google Scholar
• Vorbruggen , H. and Woodward , R. B. 1993 . The conversion of β‐amino esters by alkylaluminium compounds into β‐lactams . Tetrahedron , 49 : 1625 [CROSSREF]
   Google Scholar