RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2010(12): 2101-2105
DOI: 10.1055/s-0029-1218763
DOI: 10.1055/s-0029-1218763
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkIntramolecular Azide-Alkyne [3+2] Cycloaddition: A Versatile Route for the Synthesis of 1,2,3-Triazole Fused Dibenzo[1,5]diazocine Derivatives
Weitere Informationen
Received
4 March 2010
Publikationsdatum:
29. April 2010 (online)
Publikationsverlauf
Publikationsdatum:
29. April 2010 (online)

Abstract
A facile synthesis of [1,2,3]triazolo dibenzo[1,5]diazocines by intramolecular Huisgen 1,3-dipolar cycloaddition of azide with alkynes has been achieved. The methodology offers clean reaction and easy isolation of products in excellent yields.
Key words
triazole - diazocine - intramolecular 1,3-dipolar cycloaddition - nitrogen heterocycle
- 1a
Huisgen R.Knorr R.Moebius L.Szeimies G. Chem. Ber. 1965, 98: 4014 - 1b
Huisgen R. In 1,3- Dipolar Cycloaddition ChemistryPadwa A. Wiley; New York: 1984. p.1-176 - 2a
Alvarez R.Valaquez S.San F.Aquaro S.De C.Penro CF.Karlsson A.Balzarini J.Camarasa MJ.
J. Med. Chem. 1994, 37: 4185 - 2b
Valquez S.Alvarez R.Perez C.Cago F.De C.Balzarini J.Camarasa MJ. Antivir. Chem. Chemother. 1998, 9: 481 - 3
Buckle DR.Rockell CJM.Smith H.Spicer BA.
J. Med. Chem. 1986, 29: 2262 - 4a
Vicentini CB.Brandolini V.Guarneri M.Giori P. Farmaco 1992, 47: 1021 - 4b
Fung-Tomc JC.Huczko E.Minassian B.Bonner DP. Antimicrob. Agents Chemother. 1998, 42: 313 - 5
Palhagen S.Canger R.Henriksen O.van Paryes JA.Riviere ME.Karolchyk MA. Epilepsy Res. 2001, 43: 115 - 6
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 - 7
Bourne Y.Kolb HC.Radic Z.Sharpless KB.Taylor P.Marchot P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 1449 - 8
Fan W.-Q.Katritzky AR. In Comprehensive Heterocyclic Chemistry II Vol. 4:Katritzky AR.Rees CW.Scriven EFV. Elsevier; Oxford: 1996. p.1-26 - Recent examples:
- 9a
Didier D.Sergeyev S. Eur. J. Org. Chem. 2007, 3905 - 9b
Yuan C.-X.Tao X.-T.Ren Y.Li Y.Yang J.-X.Yu W.-T.Wang L.Jiang M.-H. J. Phys. Chem. C 2007, 111: 12811 - 10
Leganza A.Bezze C.Zonta C.Fabris F.DeLucchi O.Linden A. Eur. J. Org. Chem. 2006, 2987 - 11
Paudler WW.Zeiler AG. J. Org. Chem. 1969, 34: 2138 - See, for example:
- 12a
Nakayama T.Harada N.Asano M.Nomura N.Saito T.Mishima A.Okajima K.
J. Pharmacol. Exp. Ther. 2007, 322: 582 - 12b
Culmsee C.Gerling N.Landshamer S.Rickerts B.Duchstein HJ.Umezawa K.Klumpp S.Krieglstein J. Mol. Pharmacol. 2005, 68: 1006 - 12c
Yoshida H.Shirakawa E.Honda Y.Hiyama T. Angew. Chem. Int. Ed. 2002, 41: 3247 - 13
Rostovtsev VV.Green LG.Fokin VV.Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596 - 14a
Tornøe CW.Meldal M. Peptidotriazoles: Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions on Solid Phase, In The Wave of the FutureLebl M.Houghten RA. American Peptide Society; San Diego: 2001. p.263 - 14b
Tornøe CW.Christensen C.Meldal M. J. Org. Chem. 2002, 67: 3057 - 15a
Boren BC.Narayan S.Rasmussen LK.Zhang L.Zhao H.Lin Z.Jia G.Fokin VV. J. Am. Chem. Soc. 2008, 130: 8923 - 15b
Zhang L.Chen X.Xue P.Sun HHY.Williams ID.Sharpless KB.Fokin VV.Jia G. J. Am. Chem. Soc. 2005, 127: 15998 - 16a
Link AJ.Tirrell DA. J. Am. Chem. Soc. 2003, 125: 11164 - 16b
Wang Q.Chan TR.Hilgraf R.Fokin VV.Sharpless KB.Finn MG. J. Am. Chem. Soc. 2003, 125: 3192 - 16c
Speers AE.Cravatt BF. Chem. Biol. 2004, 11: 535 - 16d
Lee LV.Mitchel ML.Huang S.-J.Fokin VV.Sharpless KB.Wong C.-H. J. Am. Chem. Soc. 2003, 125: 9588 - 17a
Hu TS.Tannert R.Arndt HD.Waldmann H. Chem. Commun. 2007, 3942 - 17b
Turner RA.Oliver AG.Lokey RS. Org. Lett. 2007, 9: 5011 - 18a
Zhang X.Hsung RP.Li H. Chem. Commun. 2007, 2420 - 18b
Bertrand P.Gesson J.-P. J. Org. Chem. 2007, 72: 3596 - 18c
Majumdar KC.Mondal S. Lett. Org. Chem. 2009, 6: 82 - 19
Kumar D.Reddy VB.Varma RS. Tetrahedron Lett. 2009, 50: 2065 - 20a
Beckmann HSG.Wittmann V. Org. Lett. 2004, 9: 1 - 20b
Tao C.-Z.Cui X.Li J.Liu A.-X.Liu L.Guo Q.-X. Tetrahedron Lett. 2007, 48: 3525 - 20c
Barral K.Moorhouse AD.Moses JE. Org.Lett. 2007, 9: 1809 - 21
Harju K.Vahermo M.Mutikainen I.Kauhaluoma JY. J. Comb. Chem. 2003, 5: 826 - 22a
Corres N.Delgado JJ.Garcia-Valverde M.Marcaccini S.Rodriguez T.Rojo J.Torroba T. Tetrahedron 2008, 64: 2225 - 22b
Klapars A.Parris S.Anderson KW.Buchwald SL. J. Am. Chem. Soc. 2004, 126: 3529 - 22c
Jung DI.Song JH.Lee EJ.Kim YY.Lee DH.Lee YG.Hahn JT. Tetrahedron Lett. 2009, 50: 5805 - 23
Majumdar KC.Ray K.Ganai S.Ghosh T. Synthesis 2010, 858 - 24a
Arkitopoulou-Zane I.Gracias V.Djuric SW. Tetrahedron Lett. 2004, 45: 8439 - 24b
Couty F.Durrat F.Primm D. Tetrahedron Lett. 2004, 43: 3725 - 24c
Mahapatra DK.Maity PK.Gonnade RG.Chorgade MS.Gurgar MK. Synlett 2007, 1893 - 24d
Ko SH.Lee K.-J. J. Heterocycl. Chem. 2004, 41: 613 - 24e
Pokorski JK.Miller Jenkins LM.Feng H.Durell SR.Bal Y.Applla DH. Org. Lett. 2007, 9: 2381 - 24f
Kumar I.Rode CV. Chem. Lett. 2007, 36: 592 - 24g
Beryozkina T.Appukkuttan P.Mont N.Eycken EVD. Org. Lett. 2006, 11: 487 - 25a
Hotha S.Anegundi RI.Natu AA. Tetrahedron Lett. 2005, 46: 4585 - 25b
Chandrasekhar S.Rao CL.Nagesh C.Reddy CR.Sridhar B. Tetrahedron Lett. 2007, 48: 5869 - 25c
Yanai H.Taguchi T. Tetrahedron Lett. 2005, 46: 8639 - 26
Sudhir VS.Nasir Bag RB.Chandrasekaran S. Eur. J. Org. Chem. 2008, 2423 - 27
Füger B.Sklute G.Marek I.Bolm GY.Bolm C. Synlett 2008, 116