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Synthesis 2012(8): 1253-1257
DOI: 10.1055/s-0031-1289736
DOI: 10.1055/s-0031-1289736
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Trinitromethyl- and Dinitromethyl-Substituted Azoles Using Nitrate Salts in Sulfuric Acid
Further Information
Received
1 February 2012
Publication Date:
05 March 2012 (online)
Publication History
Publication Date:
05 March 2012 (online)
Abstract
Synthesis of trinitromethyl and dinitromethyl-substituted azoles employing a mild and efficient nitration method has been developed using a mixture of sulfuric acid and an inorganic nitrate salt XNO3, where X = NH4 +, Na+, K+. This methodology exhibits clear advantages over the more popular mixed acids nitration approach. Various nitro functionalities such as C-trinitromethyl, N-trinitromethyl, and dinitromethyl ester containing azoles were prepared in moderate to excellent yields with reduced reaction times using this method.
Key words
nitrate salts - mixed acids - nitration - polynitroazoles - trinitromethyls - energetic materials
-
1a
Ducry L.Roberge DM. Angew. Chem. Int. Ed. 2005, 44: 7972 ; Angew. Chem. 2005, 117, 8186 -
1b
Ono N. The Nitro Group in Organic Synthesis Wiley; New York: 2001. -
1c
Barrett AG.Graboski GG. Chem. Rev. 1986, 86: 751 -
1d
Nagpal A.Valley MP.Fitzpatrick PF.Orville AM. Biochemistry 2006, 45: 1138 -
1e
Garg S.Gao H.Joo Y.-H.Parrish DA.Shreeve JM. J. Am. Chem. Soc. 2010, 132: 8888 -
1f
Joo Y.-H.Shreeve JM. J. Am. Chem. Soc. 2010, 132: 15081 - 2
Gao H.Ye C.Gupta OD.Hiskey MA.Twamley B.Shreeve JM. Chem. Eur. J. 2007, 13: 3853 -
3a
Kamlet MJ.Jacobs SJ. J. Chem. Phys. 1968, 48: 23 -
3b
Kamlet MJ.Ablard JE. J. Chem. Phys. 1968, 48: 36 -
4a
Köhler J.Meyer R. Explosivstoffe 7th ed.: VCH; Weinheim: 1991. -
4b
Huynh M.-HV.Hiskey MA.Hartline EL.Montoya DP.Gilardi R. Angew. Chem. Int. Ed. 2004, 43: 4924 ; Angew. Chem. 2004, 116, 5302 -
5a
Gao H.Shreeve JM. Chem. Rev. 2011, 111: 7377 -
5b
Bulusu S.Damavarapu R.Autera JR.Behrens R.Minier LM.Villanueva J.Jayasuriay K.Axenord T. J. Phys. Chem. 1995, 99: 5009 -
5c
Miner L.Behrens R.Bulusu S. J. Mass Spectrom. 1996, 31: 25 -
5d
Katritzky AR.Cundy DJ.Chen J. J. Energ. Mater. 1993, 11: 345 -
5e
Rice BM.Hare JJ. J. Phys. Chem. A 2002, 106: 1770 -
5f
Fried LE.Manaa MR.Pagoria PF.Simpson RL. Annu. Rev. Mater. Res. 2001, 31: 291 - 6
Agrawal JP.Hodgson RD. Organic Chemistry of Explosives Wiley; West Sussex: 2007. -
7a
Larina L.Lopyrev V. Nitrazoles: Synthesis Structure and Application 1st ed.: Springer; Berlin: 2009. -
7b Makosza M.; Pure Appl. Chem.; 1997, 69: 559
-
7c
Olah GA.Malhotra R.Narang SC. Nitration: Methods and Mechanisms VCH; Weinheim: 1989. - 8
Urbanski T. Chemistry and Technology of Explosives Vol. 1 and Vol. 3: Pergamon Press; New York: 1964. and references cited therein - 9
Straessler NA. Synth. Commun. 2010, 40: 2513 -
10a
Hill ME.Taylor F. J. Org. Chem. 1960, 25: 1037 -
10b
Dacons JC.Taylor F. J. Chem. Eng. Data 1969, 14: 499 -
10c
Lu L.Ou Y.Wang J. Jingxi Huagong 2004, 21: 321 ; Chem. Abstr. 2004, 141, 159368 -
11a
Thottempudi V.Shreeve JM. J. Am. Chem. Soc. 2011, 133: 19982 -
11b
Thottempudi V.Gao H.Shreeve JM. J. Am. Chem. Soc. 2011, 133: 6464 - 12
Thottempudi V.Kim TK.Chung K.-H.Kim JS. Bull. Korean Chem. Soc. 2009, 30: 2152 - 13
Lim CH.Hong S.Chung K.-H.Kim JS.Cho JR. Bull. Korean Chem. Soc. 2008, 29: 1415 - 14
Dippold AD.Klapötke TM. Z. Anorg. Allg. Chem. 2011, 637: 1453 - 15
Kofman TP.Yu G.Kartseva GYu.Glazkova EYu.Krasnov KN. Russ. J. Org. Chem. 2005, 41: 753