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Synlett 2011(17): 2572-2576
DOI: 10.1055/s-0030-1289517
DOI: 10.1055/s-0030-1289517
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Mild and Efficient Route to 2-Azetidinones Using the Cyanuric Chloride-DMF Complex
Further Information
Received
10 June 2011
Publication Date:
06 October 2011 (online)
Publication History
Publication Date:
06 October 2011 (online)
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Abstract
Efficient conversion of Schiff bases and carboxylic acids to β-lactams can be carried out at room temperature in CH2Cl2, using a cyanuric chloride-N,N-dimethyl formamide complex. The complex is easily prepared by reaction of cyanuric chloride and DMF, an inexpensive reagent, at room temperature. Optimization of conditions and comparison of yield with cyanuric chloride were performed.
Key words
2-azetidinone - β-lactam - Staudinger reaction - cyanuric chloride - Schiff base
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Ceric H.Sindler-Kulyk M.Kovacevic M.Peric M.Zivkovic A. Bioorg. Med. Chem. 2010, 18: 3053 -
1b
Southgate R. Contemp. Org. Synth. 1994, 1: 417 -
1c
Morin RB.Gorman M. Chemistry and Biology of
β-Lactam Antibiotics Academic Press; New York (NY): 1982. -
1d
Long TE.Turos E. Curr. Med. Chem.: Anti-Infective Agents 2002, 1: 251 -
2a
IMS Health, National Prescription Audit TM 2009.
-
2b
Leng D.-H.Wang D.-X.Huang Z.-T.Wang M.-X. Org. Biomol. Chem. 2010, 8: 4736 -
3a
Xu X.Fu R.Chen J.Chen S.Bai S. Bioorg. Med. Chem. Lett. 2007, 17: 101 -
3b
Clader JW. Curr. Top. Med. Chem. 2005, 5: 243 -
3c
Kvaerno L.Werder M.Houser H.Carreira EM. J. Med. Chem. 2005, 48: 6035 -
3d
Burnett DA. Curr. Med. Chem. 2004, 11: 1873 - For reviews, see:
-
4a
Parul D.Mehta PD.Sengar NPS.Pathak AK. Eur. J. Med. Chem. 2010, 5541 -
4b
Veinberg G.Vorona M.Shestakova I.Kanepe I.Lukevics E. Curr. Med. Chem. 2003, 10: 1741 -
5a
Gerona-Navarro G.de Vega JP.Garcia-Lopez MT.Andrei G.Snoeck R.Balzarini J.De Clercq E.Gonzalez-Muniz R. Bioorg. Med. Chem. Lett. 2004, 14: 2253 -
5b
Yoakim C.Ogilvie W.Cameron DR.Chabot C.Grande-Matre C.Guse I.Hache B.Naud J.Kawai S.O’Meara JA.Plante R.Deziel R. Antiviral Chem. Chemother. 1998, 9: 379 -
5c
Yoakim C.Ogilvie WW.Cameron DR.Guse I.Hache B.Naud J.O’Mera JA.Pante R.Deziel R. J. Med. Chem. 1998, 41: 2882 -
6a
Marchand-Brynaert J.Dive G.Galleni M.Gerard S. Bioorg. Med. Chem. 2004, 12: 129 -
6b
Gerard S.Dive G.Clamet B.Touillaux R.Marchand-Brynaert J. Tetrahedron 2002, 58: 2423 -
6c
Firestone RA.Barker PL.Pisano JM.Ashe BM.Dahlgren ME. Tetrahedron 1990, 46: 2255 -
7a
Sutton JC.Bolton SA.Harti KS.Huang MH.Jacobs G.Meng W.Zhao G.Bisacchi GS. Bioorg. Med. Chem. Lett. 2004, 14: 2233 -
7b
Sutton JC.Bolton SA.Harti KS.Huang MH.Jacobs G.Meng W.Zhao G.Bisacchi GS. Bioorg. Med. Chem. Lett. 2002, 12: 3229 - 8
Bode W.Meyer E.Powers JC. Biochemistry 1989, 28: 1951 -
9a
Tozser J.Sperka T.Pitlik J.Bagossi P. Bioorg. Med. Chem. Lett. 2005, 15: 3086 -
9b
Pitlik J.Bagossi P.Jeko J.Tozser J. Pharmazie 1996, 51: 700 -
10a
Setti EL.Davis D.Janc JM.Jeffery DA.Cheung H.Yu W. Bioorg. Med. Chem. Lett. 2005, 15: 1529 -
10b
Setti EL.Davis D.Chung T.McCarter J. Bioorg. Med. Chem. Lett. 2003, 13: 2051 -
11a
Chen D.Falsetti SC.Frezza M.Milacic V.Kazi A.Cui QC.Long TE.Turos E.Ping Dou Q. Cancer Lett. 2008, 268: 63 -
11b
Kazi A.Hill R.Long TE.Kuhn DJ.Turos E.Ping Dou Q. Biochem. Pharm. 2004, 67: 365 -
11c
Banik BK.Banik I.Becker FF. Bioorg. Med. Chem. 2005, 13: 3611 -
11d
Banik BK.Becker FF.Banik I. Bioorg. Med. Chem. 2004, 12: 2523 -
11e
Banik I.Becker FF.Banik BK. J. Med. Chem. 2003, 46: 12 -
12a
O’Driscoll M.Greenhalgh K.Young A.Turos E.Dickey S.Lim DV. Bioorg. Med. Chem. 2008, 16: 7832 -
12b
Desai KG.Desai KR. Bioorg. Med. Chem. 2006, 14: 8271 -
12c
Arnoldi A.Cabrini RM.Farina G.Merlinit L. J. Agric. Food Chem. 1990, 38: 2197 - 13
Nivsarkar M.Thavaselvam D.Prasanna S.Sharma M.Kaushik MP. Bioorg. Med. Chem. Lett. 2005, 15: 1371 - 14
Zoidis G.Fytas C.Papanastasiou I.Foscolos GB.Fytas G.Padalko E.De Clercq E.Naesens L.Neyts J.Kolocouris N. Bioorg. Med. Chem. 2006, 14: 3341 - 15
Goel RK.Mahajan MP.Kulkarni SK. J. Pharm. Pharmaceut. Sci. 2004, 7: 80 - 16
Goel RK.Singh A.Naidu PS.Mahajan MP.Kulkarni SK. J. Pharm. Pharmaceut. Sci. 2005, 8: 182 - 17
Ji H.-F.Shen L.Zhang H.-Y. Biochem. Biophys. Res. Commun. 2005, 333: 661 - 18
Carr M.Greene LM.Knox AJS.David G.Lloyd DG.Zisterer DM.Meegan MJ. Eur. J. Med. Chem. 2010, 5752 -
19a
Okuyama K.-I.Momoi Y.Sugimoto K.Okano K.Tokuyama H. Synlett 2011, 73 -
19b
D’hooghe M.Mollet K.Dekeukeleire S.De Kimpe N. Org. Biomol. Chem. 2010, 8: 607 -
19c
Alcaide B.Almendros P.Luna A.Rosario Torres M. Adv. Synth. Catal. 2010, 352: 621 -
19d
Mishra RK.Coates CM.Revell KD.Turos E. Org. Lett. 2007, 9: 575 -
19e
Anand A.Bhargava G.Kumar V.Mahajan MP. Tetrahedron Lett. 2010, 51: 2312 - For a review, see:
-
19f
Alcaide B.Almendros P.Aragoncillo C. Chem. Rev. 2007, 107: 4437 -
19g
Alcaide B.Almendros P. Curr. Med. Chem. 2004, 11: 1921 -
19h
Deshmukh ARAS.Bhawal BM.Krishnaswamy D.Govande VV.Shinkre BA.Jayanthi A. Curr. Med. Chem. 2004, 11: 1889 -
19i
Alcaide B.Almendros P. Synlett 2002, 381 -
19j
Alcaide B.Almendros P. Chem. Soc. Rev. 2001, 30: 226 -
19k
Ojima I.Delaloge F. Chem. Soc. Rev. 1997, 26: 377 -
19l
Ojima I. Acc. Chem. Res. 1995, 28: 383 -
19m
Palomo C.Aizpurua JM.Ganboa I.Oiarbide M. Synlett 2001, 1813 -
19n
Palomo C.Oiarbide M. In Topics in Heterocyclic Chemistry Vol. 22:Banik BK. Springer; Berlin: 2010. p.211-259 -
20a
Hodge M.Chen O.-H.Bane S.Sharma S.Loew M.BanerjeeA .Alcaraz AA.Snyder JP.Kingston DGI. Bioorg. Med. Chem. Lett. 2009, 19: 2884 -
20b
Ge H.Spletstoser JT.Yang Y.Kayser M.Georg GI. J. Org. Chem. 2007, 72: 756 -
20c
Paik Y.Yang C.Metaferia B.Tang S.Bane S.Ravindra R.Shanker N.Alcaraz AA.Johnson SA.Schaefer J.O’Connor RD.Cegelski L.Snyder JP.Kingston DGI. J. Am. Chem. Soc. 2007, 129: 361 -
20d
Suffness M. Taxol Science and Applications CRC Press; Boca Raton (FL): 1995. - 21
Arumugam N.Raghunathan R.Shanmugaiah V.Mathivanan N. Bioorg. Med. Chem. Lett. 2010, 20: 3698 - For reviews, see:
-
22a
Alcaide B.Almendros P. Prog. Heterocycl. Chem. 2011, 22: 85 -
22b
Aranda MT.Perez-Faginas P.Gonzalez-Muniz R. Curr. Org. Synth. 2009, 6: 325 -
22c
Fu N.Tidwell TT. Tetrahedron 2008, 64: 10465 -
22d
Brandi A.Cicchi S.Cordero FM. Chem. Rev. 2008, 108: 3988 -
22e
Singh GS. Tetrahedron 2003, 59: 7631 -
22f
Ward MF. Annu. Rep. Prog. Chem., Sect. B 2000, 96: 157 -
22g
Vankoten D.Vander Steen FH. Tetrahedron 1991, 47: 7503 -
22h
Koppel GA. Small Ring Heterocycles Vol. 42: John Wiley; New York: 1983. p.219 -
22i
Isaacs NS. Chem. Soc. Rev. 1976, 5: 181 -
22j
Mukerjee AK.Srivastava RC. Synthesis 1973, 327 -
22k
Georg GI. The Organic Chemistry of β-Lactams Verlag Chemie; New York: 1993. - 23
Staudinger H. Liebigs Ann. Chem. 1907, 356: 51 -
24a
Fodor L.Csomos P.Holczbauer T.Kalman A.Csampai A.Sohar P. Tetrahedron Lett. 2011, 52: 224 -
24b
Janikowska K.Pawelska N.Makowiec S. Synthesis 2011, 69 -
24c
Dubey A.Srivastava SK.Srivastava SD. Bioorg. Med. Chem. Lett. 2011, 21: 569 -
24d
Feroci M.Chiarotto I.Orsinib M.Inesi A. Chem. Commun. 2010, 46: 4121 -
24e
Keri RS.Hosamani KM.Shingalapur RV.Reddy HRS. Eur. J. Med. Chem. 2009, 5123 -
24f
Upadhyay A.Srivastava SK.Srivastava SD.Yadav R. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2011, 50: 89 -
24g
Keri RS.Hosamani KM. Monatsh. Chem. 2010, 141: 883 -
24h
Dekeukeleire S.D’hooghe M.Muller C.Vogt D.De Kimpe N. New J. Chem. 2010, 34: 1079 -
24i
Coates C.Kabir J.Turos E. Science of Synthesis Vol. 21:Weinreb SM. Thieme; Stuttgart: 2005. p.609-646 -
24j
Jarrahpour A.Motamedifar M.Zarei M.Mimouni M. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185: 287 -
24k
Jarrahpour A.Zarei M. Molecules 2006, 11: 49 -
24l
Jarrahpour A.Khalili D. Tetrahedron Lett. 2007, 48: 7140 -
24m
Jarrahpour A.Ebrahimi E. Molecules 2010, 15: 515 -
24n
Hakimelahi GH.Jarrahpour AA. Helv. Chim. Acta 1989, 72: 1501 -
24o
Jarrahpour A.Fadavi A.Zarei M. Bull. Chem. Soc. Jpn. 2011, 84: 320 -
25a
Qi H.Yang Z.Xu J. Synthesis 2011, 723 -
25b
Tidwell TT. Ketenes II John Wiley and Sons; Hoboken (NJ): 2006. p.55-192 -
25c
Tidwell TT. Eur. J. Org. Chem. 2006, 563 -
26a
Banik BK.Banik I.Becker FF. Eur. J. Med. Chem. 2010, 846 -
26b
O’Boyle NM.Carr M.Greene LM.Bergin O.Nathwani SM.McCabe T.Lloyd DG.Zisterer DM.Meegan MJ. J. Med. Chem. 2010, 53: 8569 -
26c
Jarrahpour A.Zarei M. Tetrahedron 2010, 66: 5017 -
26d
Jarrahpour A.Zarei M. Tetrahedron Lett. 2009, 50: 1568 -
26e
Jarrahpour A.Zarei M. Tetrahedron 2009, 65: 2927 -
26f
Nahmany M.Melman A. J. Org. Chem. 2006, 71: 5804 -
26g
Vatmurge NS.Hazra BG.Pore VS.Shirazi F.Chavan PS.Deshpande MV. Bioorg. Med. Chem. Lett. 2008, 18: 2043 -
26h
Bose AK.Manhas MS.Amin SG.Kapur JC.Kreder J.Mukkavilli L.Ram B.Vincent JE. Tetrahedron Lett. 1979, 20: 2771 -
26i
Bose AK.Kapur JC.Sharma SD.Manhas MS. Tetrahedron Lett. 1973, 2319 -
26j
Jarrahpour A.Zarei M. Molecules 2007, 12: 2364 -
26k
Bhalla A.Venugopalany P.Bari SS. Tetrahedron 2006, 62: 8291 -
26l
Manhas MS.Bose AK.Khajavi MS. Synthesis 1981, 209 -
26m
Matsui S.Hashimoto Y.Saigo K. Synthesis 1998, 1161 -
26n
Croce PD.La Rosa C. Tetrahedron: Asymmetry 1999, 10: 1193 -
26o
Sharma SD.Kanwar S. Org. Process Res. Dev. 2004, 8: 658 -
26p
Jarrahpour A.Zarei M. Tetrahedron Lett. 2007, 48: 8712 -
26q
Isobe T. J. Org. Chem. 1999, 64: 6989 -
26r
Bhalla A.Nagpal Y.Kumar R.Mehta SK.Bhasin KK.Bari SS. J. Organomet. Chem. 2009, 694: 179 -
26s
Meshram J.Ali P.Tiwari V.
J. Heterocycl. Chem. 2010, 47: 1454 -
26t
Arrieta A.Aizpurua JM.Palomo C. Tetrahedron Lett. 1984, 25: 3365 -
26u
Palomo C.Aizpurua JM.Urchegui R.Iturburu M.de Retana AO.Cuevas C. J. Org. Chem. 1991, 56: 2244 -
27a
Giacomelli G.Porcheddu A.De Luca L. Curr. Org. Chem. 2004, 8: 1497 -
27b
Haval KP. Synlett 2006, 2156 -
27c
Blotny G. Tetrahedron 2006, 62: 9507 -
27d
Zhang Z.-H.Tao X.-Y. Aust. J. Chem. 2008, 61: 77 -
28a
Van der Veen JM.Bari SS.Krishnan L.Manhas MS.Bose AK. J. Org. Chem. 1989, 54: 5758 -
28b
Wagle DR.Garai C.Chiang J.Monteleone MG.Kurys BE.Strohmeyer TW.Hegde VR.Manhas MS.Bose AK. J. Org. Chem. 1988, 53: 4227 - 29
Gold H. Angew. Chem. 1960, 72: 956 - 30
De Luca L.Giacomelli G.Porcheddu A. J. Org. Chem. 2002, 67: 5152 - 31
De Luca L.Giacomelli G.Porcheddu A. J. Org. Chem. 2002, 67: 6272 - 32
De Luca L.Giacomelli G.Porcheddu A. Org. Lett. 2002, 4: 553 - 33
Chang C.-W.Chang S.-S.Chao C.-S.Mong K.-KT. Tetrahedron Lett. 2009, 50: 4536