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 2008(5): 699-706
DOI: 10.1055/s-2008-1032187
DOI: 10.1055/s-2008-1032187
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Dinitro-Substituted Furans, Thiophenes, and Azoles
Weitere Informationen
Received
27 September 2007
Publikationsdatum:
18. Februar 2008 (online)
Publikationsverlauf
Publikationsdatum:
18. Februar 2008 (online)
Abstract
Direct nitration of the corresponding mononitro furans with fuming nitric acid, thiophenes with acetyl nitrate, and thiazoles with trifluoroacetyl nitrate, gave dinitro-substituted furans, thiophenes, and thiazoles. The nitrations of 2-alkylthiophenes with 3 and 5 molar equivalents of acetyl nitrate, generated in situ, are discussed. Reactions of the mononitro furans with fuming nitric acid gave 1,1,5,5-tetrasubstituted dihydrofurans as by-products. Treatment of 5-methyl-4-nitroisoxazole with hydrazine or its methyl or phenyl derivative, followed by oxidation of the corresponding 4-amino-5-nitro-1H-pyrazoles with hydrogen peroxide (50%) gave 4,5-dinitro-1H-pyrazoles. A safe one-pot synthesis of 1-alkyl-3,5-dinitro-1H-[1,2,4]triazoles was developed from dicyandiamide.
Key words
dinitrofurans - dinitrothiophenes - dinitroazoles - nitration - oxidation
- 1
Agrawal KC.Bears KB.Sehgal RK.Brown JN.Rist PE.Rupp WD. J. Med. Chem. 1979, 22: 583 - 2
Padwa A.Waterson AG. ARKIVOC 2001, (iv): 29 - 3
Blatt AH.Bach S.Kresch LW. J. Org. Chem. 1957, 22: 1693 - 4
Godovikova TI.Rakitin OA.Golova SP.Vozchikova SA.Povorin MV.Khmel’nitskii LI. Chem. Heterocycl. Compd. (Engl. Transl.) 1994, 30: 465 -
5a
Kofman TP.Paketina EA. Russ. J. Org. Chem. (Engl. Transl.) 1997, 33: 1125 -
5b
Millar RW.Claridge RP.Sandall JPB.Thompson C. ARKIVOC 2002, (iii): 19 - 6
Katritzky AR.Fan W.-Q. Heterocycles 1992, 34: 2179 - 7
Katritzky AR.Cundy DJ.Chen J. J. Energetic Mater. 1993, 11: 345 - 8
Katritzky AR.Cundy DJ.Chen J. J. Heterocycl. Chem. 1994, 31: 271 - 9
Katritzky AR.Scriven EFV.Majumder S.Akhmedova RG.Vakulenko AV.Akhmedov NG.Murugan R.Abboud KA. Org. Biomol. Chem. 2005, 3: 538 - 10
Katritzky AR.Scriven EFV.Majumder S.Akhmedova RG.Akhmedov NG.Vakulenko AV. ARKIVOC 2005, (iii): 179 - 11
Doddi G.Stegel F.Tanasi MT. J. Org. Chem. 1978, 43: 4303 - 12
Scully JF.Brown EV. J. Org. Chem. 1954, 19: 894 -
13a
Schuisky P.Twistel W.Grivas S. Heterocycles 1998, 48: 1431 -
13b
Saldabol N.Slavinskaya V.Popelis Yu.Mazheika I. Chem. Heterocycl. Compd. (Engl. Transl.) 2000, 36: 134 - 14
Norris RK. Chem. Heterocycl. Compd. (Engl. Transl.) 1986, 22: 523 - 15
Meyer V.Stadler O. Ber. Dtsch. Chem. Ges. 1884, 17: 2648 - 16
Francis F. Ber. Dtsch. Chem. Ges. 1906, 39: 3798 - 17
Pictet A.Khotinsky E. Ber. Dtsch. Chem. Ges. 1907, 40: 1163 - 18
Steinkopf W. Justus Liebigs Ann. Chem. 1914, 403: 17 - 19
Rajappa S.Advani BG.Sreenivasan R. Synthesis 1974, 656 - 20
Guk YV.Ilyushin MA.Golod EL.Gidaspov BV. Russ. Chem. Rev. (Engl. Transl.) 1983, 52: 284 - 21
Babasinian VS. J. Am. Chem. Soc. 1928, 50: 2748 - 22
Östman B. Acta Chem. Scand. 1968, 22: 2754 - 23
Newcombe PJ.Norris RK. Aust. J. Chem. 1978, 31: 2463 -
24a
Rinkes IJ. Recl. Trav. Chim. Pays-Bas 1932, 51: 1134 -
24b
Hardy GW.Lowe LA.Mills G.Sang PY.Simpkin DSA.Follenfant RL.Shankley C.Smith TW. J. Med. Chem. 1989, 32: 1108 -
24c
Pinkin LD.Zhiryakov VG. Chem. Heterocycl. Compd. (Engl. Transl.) 1983, 19: 833 - 25
Khalaf AI.Ebrahimabadi AH.Drummond AJ.Anthony NG.Mackay SP.Suckling CJ.Waigh RD. Org. Biomol. Chem. 2004, 2: 3119 - 26
Gronowitz S.Gjøs N. Acta Chem. Scand. 1967, 21: 2823 - 27
Snyder HR.Carpino LA.Zack JF.Mills JF. J. Am. Chem. Soc. 1957, 79: 2556 - 28
Gronowitz S.Ander I. Acta Chem. Scand., Ser. B 1975, 29: 513 -
29a
Jiang B.Tilley D. J. Am. Chem. Soc. 1999, 121: 9744 -
29b
Mahammed A.Gross Z. J. Am. Chem. Soc. 2005, 127: 2883 - 30
Parent RA. J. Org. Chem. 1962, 27: 2282 - 31
Prijs B.Mengisen W.Fallab S.Erlenmeyer H. Helv. Chim. Acta 1952, 35: 187 - 32
Huttel R.Buchele F.Jochum P. Chem. Ber. 1955, 88: 1577 - 33
Janssen JWAM.Koeners HJ.Kruse CG.Habraken CL. J. Org. Chem. 1973, 38: 1777 - 34
Grimmett MR.Lim KHR. Aust. J. Chem. 1978, 31: 689 - 35
Andreeva MA.Manaev YuA.Mushii RYa.Perevalov VP.Seraya VI.Stepanov BI. J. Gen. Chem. USSR (Engl. Transl.) 1980, 50: 1705 - 36
Chang K.-C.Grimmett MR.Ward DD.Weavers RT. Aust. J. Chem. 1979, 32: 1727 - 37
Alberola A.Antolin LF.Gonzalez AM.Laguna MA.Pulido FJ. J. Heterocycl. Chem. 1986, 23: 1035 -
38a
Zhang Yu.Chu T.Gao X.Liu X.Yang Z.Guo Z.Wang X. Bioorg. Med. Chem. Lett. 2006, 16: 1831 -
38b
Das T.Chakraborty S.Banerjee S.Mukherjee A.Samuel G.Sarma HD.Nair CKK.Kagiya VT.Venkatesh M. Bioorg. Med. Chem. 2004, 12: 6077 - 39
Toriyabe K,Yamaguchi M,Itou Y,Kinpara S,Yano H,Takahashi S,Yonekura N, andHamaguchi R. inventors; WO2006043635, . ; Chem. Abstr. 2006, 144, 432816 - 40
Le Campion L.Giannotti C.Ouazzani J. Chemosphere 1999, 38: 1561 -
41a
Jalovy Z.Vavra P. Sci. Pap. Univ. Pardubice, Ser. A.: Fac. Chem. Technol. 2004, 9: 187 ; Chem. Abstr. 2004, 141, 142755 -
41b
Walsh CM,Knott CD, andLeveritt CS. inventors; US Patent 6984275. ; Chem. Abstr. 2006, 144, 90622 - 42
Ou Y.Chen B.Li J.Dong S.Li J.Jia H. Heterocycles 1994, 38: 1651 - 43
Katritzky AR.Lagowski JM. In Comprehensive Heterocyclic Chemistry Vol. 5:Katritzky AR.Rees CW. Pergamon Press; Oxford: 1984. p.752 - 44
Katritzky AR.Ögretir C. Chim. Acta Turcica 1982, 10: 137 ; Chem. Abstr. 1982, 98, 159930 - 45
Chernyshev VM.Zemlyakov ND.Il’in VB.Taranushich VA. Zh. Prikl. Khim. 2000, 73: 791 ; Chem. Abstr. 2000, 133, 252376 -
46a
Burchfield HP, andGullstrom DK. inventors; US Patent 3054800. ; Chem. Abstr. 1963, 58, 59822 -
46b
Bagal LI.Pevzner MS.Sheludyakova NI.Kerusov VM. Chem. Heterocycl. Compd. (Engl. Transl.) 1970, 6: 245 - 47
Pevzner MS.Timofeeva TN.Gorbunova NN.Frolova GM. J. Org. Chem. USSR (Engl. Transl.) 1976, 12: 1352 - 48
Bagal LI.Pevzner MS.Egorov AP.Samarenko VYa. Chem. Heterocycl. Compd. (Engl. Transl.) 1970, 6: 928 - 49
von Philipsborn W.Müller R. Angew. Chem., Int. Ed. Engl. 1986, 25: 386 - 50
Pérez JD.Wunderlin DA. J. Org. Chem. 1987, 52: 3637 - 51
Stillman WB,Scott AB, andClampit JM. inventors; German Patent DE 974602. ; Chem. Abstr. 1962, 57, 10808 -
52a
Camaggi CM.Leardino R.Placucci G. J. Chem. Soc., Perkin Trans. 2 1974, 1195 -
52b
Vakhreeva KI.Gusarov AN.Zvolinskii VP.Zemtsova MN.Zimichev AV.Lipkin AE.Sharonov KG.Yudashkin AV. Tezisy Dokl. 14th Nauchn. Sess. Khim. Tekhnol. Org. Soedin. Sery Sernistykh NefteiBakhtalze IG. Zintane; Riga, USSR: 1976. p.192-193 ; Chem. Abstr. 1978, 89, 6169 - 53
Gol’dfarb YaL.Fabrichnyi BP.Shalavina IF. J. Gen. Chem. USSR (Engl. Transl.) 1959, 29: 3596 - 54
Borgen G.Gronowirz S.Dahlbom R.Holmberg B. Acta Chem. Scand. 1966, 20: 2593 - 55
Prijs B.Ostertag J.Erlenmeyer H. Helv. Chim. Acta 1947, 30: 1200