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Synthesis 2009(10): 1708-1714
DOI: 10.1055/s-0029-1216786
DOI: 10.1055/s-0029-1216786
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Efficient Synthesis of Azo Dye Labeled Terpenes, Sugars, and Steroids Using N-(4-Arylazobenzoyl)-1H-benzotriazoles
Further Information
Received
13 November 2008
Publication Date:
27 April 2009 (online)
Publication History
Publication Date:
27 April 2009 (online)
Abstract
N-(4-Arylazobenzoyl)-1H-benzotriazoles react with hydroxyterpenes, sugars, and steroids in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature in tetrahydrofuran to afford azo dye labeled terpenes, sugars, and steroids (45-82% yield).
Key words
azo dyes - acylations - steroids - sugars - terpenes
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1a
Natansohn A.Rochon P. Chem. Rev. 2002, 102: 4139 -
1b
Pieroni O.Fissi A.Angelini N.Lenci F. Acc. Chem. Res. 2001, 34: 9 -
1c
Ichimura K. Chem. Rev. 2000, 100: 1847 -
1d
Leclair S.Mathew L.Giguere M.Motallebi S.Zhao Y. Macromolecules 2003, 36: 9024 -
1e
Nakatsuji S.Fujino M.Hasegawa S.Akutsu H.Yamada J.-i.Gurman VS.Vorobiev AKh. J. Org. Chem. 2007, 72: 2021 -
1f
Philip B.Sreekumar K. J. Polym. Sci.: Part A: Polym. Chem. 2002, 40: 2868 -
2a
Koshi Y.Nakata E.Yamane H.Hamachi I. J. Am. Chem. Soc. 2006, 128: 10413 -
2b
Bergbreiter DE.Osburn PL.Li C. Org. Lett. 2002, 4: 737 -
2c
Bergbreiter DE.Li C. Org. Lett. 2003, 5: 2445 -
2d
Wang LS.Birembaut F.Brocklesby WS.Frey JG.Bradley M. Anal. Chem. 2005, 77: 2247 -
3a
Kubota M.Ono A. Tetrahedron Lett. 2004, 45: 5755 -
3b
Asanuma H.Shirasuka K.Takarada T.Komiyama M. J. Am. Chem. Soc. 2003, 125: 2217 -
4a
Rose TM.Prestwich GD. Org. Lett. 2006, 8: 2575 -
4b
Grossmann TN.Seitz O. J. Am. Chem. Soc. 2006, 128: 15596 -
5a
Yang CJ.Martinez K.Lin H.Tan W. J. Am. Chem. Soc. 2006, 128: 9986 -
5b
Yang CJ.Martinez K.Lin H.Tan W. J. Am. Chem. Soc. 2005, 127: 12772 -
5c
Wang L.Yang CJ.Medley CD.Benner SA.Tan W. J. Am. Chem. Soc. 2005, 127: 15664 -
5d
Tan L.Li Y.Drake TJ.Moroz L.Wang K.Li J.Munteanu A.Yang CJ.Martinez K.Tan W. Analyst (Cambridge, U.K.) 2005, 130: 1002 -
5e
Gunnlaugsson T.Kelly JM.Nieuwenhuyzen M.O’Brien MK. Tetrahedron Lett. 2003, 44: 8571 -
5f
Maung J.Mallari JP.Girtsman TA.Wu LY.Rowley JA.Santiago NM.Brunelle AN.Berkman CE. Bioorg. Med. Chem. 2004, 12: 4969 -
6a
Apreutesei D.Lisa G.Hurduc N.Scutaru D. J. Therm. Anal. Calorim. 2006, 83: 335 -
6b
Apreutesei D.Lisa G.Akutsu H.Hurduc N.Nakatsuji S.Scutaru D. Appl. Organomet. Chem. 2005, 19: 1022 -
7a
Kazutara M.Aoki M.Nishi T.Ikeda A.Shinkai S. J. Chem. Soc., Chem. Commun. 1991, 1715 -
7b
Ono Y.Nakashima K.Sano M.Hojo J.Shinkai S. J. Mater. Chem. 2001, 11: 2412 -
7c
Murata K.Aoki M.Suzuki T.Harada T.Kawabata H.Komori T.Ohseto F.Ueda K.Shinkai S. J. Am. Chem. Soc. 1994, 116: 6664 -
8a
Bobrovsky AY.Boiko NI.Shibaev VP.Springer J. Liq. Cryst. 2001, 28: 919 -
8b
Liu J.-H.Wang H.-Y. J. Appl. Polym. Sci. 2004, 91: 789 -
9a
Coleman GH.Rees DE.Sundberg RL.McCloskey CM. J. Am. Chem. Soc. 1945, 67: 381 -
9b
Srinivas O.Mitra N.Surolia A.Jayaraman N. J. Am. Chem. Soc. 2002, 124: 2124 - 10
Liu X.-M.Yang B.Wang Y.-L.Wang J.-Y. Biochim. Biophys. Acta Biomembr. 2005, 1720: 28 - 11
Gunnlaugsson T.Kelly JM.Nieuwenhuyzen M.O’Brien AMK. Tetrahedron Lett. 2003, 44: 8571 - 12
Nutting WH.Jewell RA.Rapoport H. J. Org. Chem. 1970, 35: 505 -
13a
Katritzky AR.Suzuki K.Wang Z. Synlett 2005, 1656 -
13b
Katritzky AR.Angrish P.Suzuki K. Synthesis 2006, 411 -
13c
Katritzky AR.Angrish P.Hur D.Suzuki K. Synthesis 2005, 397 -
13d
Katritzky AR.Suzuki K.Singh SK.He H.-Y. J. Org. Chem. 2003, 68: 5720 -
13e
Katritzky AR.He H.-Y.Suzuki K. J. Org. Chem. 2000, 65: 8210 -
13f
Katritzky AR.Wang M.Yang H.Zhang S.Akhmedov NG. ARKIVOC 2002, (viii): 134 -
13g
Katritzky AR.Shestopalov AA.Suzuki K. ARKIVOC 2005, (vii): 36 -
13h
Katritzky AR.Tala SR.Singh SK. Synthesis 2006, 3231 -
14a
Katritzky AR.Belyakov SA. Aldrichimica Acta 1998, 31: 35 -
14b
Katritzky AR.Li J.Xie J. Tetrahedron 1999, 55: 8263 - 15
Katritzky AR.Chen Q.-Y.Tala SR. Org. Biomol. Chem. 2008, 6: 2400