Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2010(5): 858-862
DOI: 10.1055/s-0029-1218610
DOI: 10.1055/s-0029-1218610
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkCatalyst-Free 1,3-Dipolar Cycloaddition: An Efficient Route for the Formation of the 1,2,3-Triazole-Fused Diazepinone Framework
Further Information
Received
2 November 2009
Publication Date:
16 December 2009 (online)
Publication History
Publication Date:
16 December 2009 (online)
Abstract
A catalyst-free, effective method for the synthesis of the hitherto unreported 1,2,3-triazole-fused diazepinone framework in good to excellent yield through 1,3-dipolar cycloaddition is reported. The generality of the reaction is demonstrated by the synthesis of an array of [1,2,3]triazolodiazepinones. The methodology offers a clean reaction and easy isolation of the products in good to excellent yield.
Key words
triazoles - diazepinones - 1,3-dipolar cycloaddition
- 1a
Alvarez R.Velázquez S.San-Félix A.Aquaro S.De Clercq E.Perno C.-F.Karlsson A.Balzarini J.Camarasa MJ. J. Med. Chem. 1994, 37: 4185MissingFormLabel - 1b
Velázquez S.Alvarez R.Pérez C.Gago F.De Clercq E.Balzarini J.Camarasa MJ. Antiviral Chem. Chemother. 1998, 9: 481MissingFormLabel - 2
Buckle DR.Rockell CJM.Smith H.Spicer BA. J. Med. Chem. 1986, 29: 2262 - 3a
Vicentini CB.Brandolini V.Guarneri M.Giori P. Farmaco 1992, 47: 1021MissingFormLabel - 3b
Fung-Tomc JC.Huczko E.Minassian B.Bonner DP. Antimicrob. Agents Chemother. 1998, 42: 313MissingFormLabel - 4
Palhagen S.Canger R.Henriksen O.van Parys JA.Riviere M.-E.Karolchyk MA. Epilepsy Res. 2001, 43: 115 - 5
Genin MJ.Allwine DA.Anderson DJ.Barbachyn MR.Emmert DE.Garmon SA.Graber DR.Grege KC.Hester JB.Hutchinson DK.Morris J.Reischer RJ.Ford CW.Zurenko GE.Hamel JC.Schaadt RD.Stapert D.Yagi BH. J. Med. Chem. 2000, 43: 953 - 6
Fan W.-Q.Katritzky AR. In Comprehensive Heterocyclic Chemistry II Vol. 4:Katritzky AR.Rees CW.Scriven EFV. Elsevier Science; Oxford: 1996. p.1-26 - 7a
Huisgen R.Szeimies G.Moebius L. Chem. Ber. 1967, 100: 2494MissingFormLabel - 7b
Huisgen R. 1,3-Dipolar Cycloaddition Chemistry Wiley & Sons; New York: 1984. p.1-176MissingFormLabel - 7c
Huisgen R. Pure Appl. Chem. 1989, 61: 613MissingFormLabel - 8a
Arkitopoulou-Zane I.Gracias V.Djuric SW. Tetrahedron Lett. 2004, 45: 8439MissingFormLabel - 8b
Couty F.Durrat F.Prim D. Tetrahedron Lett. 2004, 45: 3725MissingFormLabel - 8c
Mahapatra DK.Maity PK.Gonnade RG.Chorgade MS.Gurgar MK. Synlett 2007, 1893MissingFormLabel - 8d
Rohr W.Fischer A.Bad A.Sodafabr A.-G. In Pesticide Chemistry: Proceedings of the Second International IUPAC Congress Vol. 5:Tahori AS. Gordon & Breach; New York: 1972. p.177MissingFormLabel - 8e
Pokorski JK.Millers Jenkins LM.Feng H.Durell SR.Bai Y.Appella DH. Org. Lett. 2007, 9: 2381MissingFormLabel - 8f
Kumar I.Rode CV. Chem. Lett. 2007, 36: 592MissingFormLabel - 8g
Sudhir VS.Nasir Bag RB.Chandrasekaran S. Eur. J. Org. Chem. 2008, 2423MissingFormLabel - 9a
Hotha S.Anegundi RI.Natu AA. Tetrahedron Lett. 2005, 46: 4585MissingFormLabel - 9b
Chandrasekhar S.Rao CL.Nagesh C.Reddy CR.Sridhar B. Tetrahedron Lett. 2007, 48: 5869MissingFormLabel - 10a
Zhang X.Hsung RP.Li H. Chem. Commun. 2007, 2420MissingFormLabel - 10b
Bertrand P.Gesson J.-P. J. Org. Chem. 2007, 72: 3596MissingFormLabel - 10c
Majumdar KC.Mondal S. Lett. Org. Chem. 2009, 6: 82MissingFormLabel - 11
Kumar D.Reddy VB.Varma RS. Tetrahedron Lett. 2009, 50: 2065 - 12a
Beckmann HSG.Wittmann V. Org. Lett. 2007, 9: 1MissingFormLabel - 12b
Tao C.-Z.Cui X.Li J.Liu A.-X.Liu L.Guo Q.-X. Tetrahedron Lett. 2007, 48: 3525MissingFormLabel - 13
Harju K.Vahermo M.Mutikainen I.Kauhaluoma JY. J. Comb. Chem. 2003, 5: 826 - 14a
Evans BE.Rittle KE.Bock MG.DiPardo RM.Freidinger RM.Whitter WL.Lundell GF.Veber DF.Anderson PS.Chang RSL.Lotti VJ.Cerino DJ.Chen TB.Kling PJ.Kunkel KA.Springer JP.Hirshfield J. J. Med. Chem. 1988, 31: 2235MissingFormLabel - 14b
Patchett AA.Nargund RP. Annu. Rep. Med. Chem. 2000, 35: 289MissingFormLabel - 15
Sternbach LH. J. Med. Chem. 1979, 22: 1 - 16
Pritchett DB.Seeburg PH. J. Neurochem. 1990, 54: 1802 - 17
Konishi M.Hatori M.Tomita K.Sugawara M.Ikeda C.Nishiyama Y.Imanishi H.Miyaki T.Kawaguchi H. J. Antibiot. 1984, 37: 191 - 18a
Goetz MA.Lopez M.Monaghan RL.Chang RSL.Lotti VJ.Chen TB. J. Antibiot. 1985, 38: 1633MissingFormLabel - 18b
Chang RSL.Lotti VJ.Monaghan RL.Birnbaum J.Stapley EO.Goetz MA.Albers-Schönberg G.Patchett AA.Liesch JM.Hensens OD.Springer JP. Science (Washington, D.C.) 1985, 230: 177MissingFormLabel - 19a
Kim K.Volkman SK.Ellman JA. J. Braz. Chem. Soc. 1998, 9: 375MissingFormLabel - 19b
Correa A.Herrero MT.Tellitu I.Domínguez E.Moreno I.SanMartin R. Tetrahedron 2003, 59: 7103MissingFormLabel - 20
Ko SH.Lee K.-J. J. Heterocycl. Chem. 2004, 41: 613 - 21a For
a discussion of the hazards associated with azides, see: Prudent
Practice for Handling Hazardous Chemicals in Laboratories
National
Academic Press;
Washington DC:
1983.
p.87-88
MissingFormLabel
- 21b For human toxicity,
see: The Merck Index, 12th ed.
Merck & Co.;
Rahway
NJ:
1996.
4818:
p.8726
MissingFormLabel