Orthoamides and Iminium Salts LXXVII. Cycloadditions to N,N,N′,N′,N′′,N′′,N′′′,N′′′-Octamethylacetylenedicarboxamidinium Bis(tetrafluoroborate): A New Synthetic Method for the Preparation of Heterocyclic Dicarboxamidinium Salts

Konstantin Drandarov; Willi Kantlehner

doi:10.1055/s-0031-1290410

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(15): 2408-2412
DOI: 10.1055/s-0031-1290410

paper

Orthoamides and Iminium Salts LXXVII.^{[
¹
]} Cycloadditions to N,N,N′,N′,N′′,N′′,N′′′,N′′′-Octamethylacetylenedicarboxamidinium Bis(tetrafluoroborate): A New Synthetic Method for the Preparation of Heterocyclic Dicarboxamidinium Salts

Konstantin Drandarov

^aInstitut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany

,

Willi Kantlehner*

^aInstitut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany

^bFakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstr. 1, 73430 Aalen, Germany, Fax: +49(7361)5762250 eMail: willi.kantlehner@htw-aalen.de

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Abstract

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Dedicated to Professor Dr. Volker Jäger on the occasion of his 70^th birthday

Abstract

The new, hitherto unknown, heterocyclic 1,2-dicarboxamidinium salts were prepared from N,N,N′,N′,N′′,N′′,N′′′,N′′′-octamethylacetylenedicarboxamidinium bis(tetrafluoroborate) and benzyl azide, C-phenyl-N-methylnitrone, (ethoxycarbonyl)pyridiniomethanide (prepared in situ from N-[(ethoxycarbonyl)methyl]pyridinium bromide), aromatic o-hydroxycarbaldehydes salicylaldehyde and 2-hydroxy-1-naphthaldehyde, 2-[(phenylimino)methyl]phenol, methyl salicylate, and phenyldiazomethane.

Key words

cycloaddition - azide - diazoalkane - nitrone - ylide - aromatic hydroxycarbaldehyde - hydroxy imine - aromatic 2-hydroxy esters - acetylenedicarboxamidinium bis(tetrafluoroborate) - heterocyclic bis(amidinium) salts

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Referenzen

References
1 Orthoamides and Iminium Salts Part LXXVI: Kantlehner W., Vettel, M.; Eppinger, B. Z. Naturforsch. , B 2012, 67, 373

2a Bai Y, Cao Y, Zhang J, Wang M, Li R, Wang P, Zakeeruddin SM, Grätzel M. Nat. Mater. 2008; 7: 626
2b Wang P, Zakeeruddin SM, Grätzel M, Kantlehner W, Mezger H, Stoyanov EV, Scherr O. Appl. Phys. A 2004; 73

3a Iminium Salts in Organic Chemistry . In Advances in Organic Chemistry . Vol. 9/2. Böhme H, Viehe HG. Wiley; New York: 1979
3b Simchen G. Houben–Weyl . Vol. 5/1. Falbe J. Georg Thieme Verlag; Stuttgart: 1985: 88-104
3c Kantlehner W. Comprehensive Organic Synthesis . Vol. 6. Fleming I, Trost BM, Winterfeldt E. Pergamon Press; Oxford: 1991: 485-599

4a Viehe HG, Baum JS. Chimia 1975; 29: 300
4b Baum JS, Viehe HG. J. Org. Chem. 1976; 41: 183

5 Maas G, Singer B, Wald P, Gimmig M. Chem. Ber. 1988; 121: 1847
6 Francois J.-P, Gittos MW. Synth. Commun. 1979; 9: 741
7 Baum JS. Postdoctoral Technical Report. UCL Louvain; Belgium: 1975
8 Kantlehner W, Lehmann H, Stahl T, Kaim W. Chem. Ztg. 1991; 115: 183
9 Nikolai J, Schlegel J, Regitz M, Maas G. Synthesis 2002; 497
10 Gerster H, Espenlaub S, Maas G. Synthesis 2006; 2251
11 Gerster H, Maas G. Z. Naturforsch., B: Chem. Sci. 2008; 636: 384
12 Kiesel M, Haug E, Kantlehner W. J. Prakt. Chem. 1997; 339: 159
13 Drandarov K, Tiritiris I, Wassiljew O, Siehl H.-U, Kantlehner W. Chem.–Eur. J. 2012; 18: 7224

14a Chapyshev SV. Chem. Heterocycl.Compd. (Engl. Transl.) 2001; 37: 861
14b Mayot E, Gerardin-Charbonnier C, Selve C. J. Fluorine Chem. 2005; 126: 715
14c Peto C, Batta G, Zoltán Györgydeák Z, Sztaricskai F. J. Carbohydr. Chem. 1996; 15: 465

15 Cheng Y, Ma B, Wudl F. J. Mater. Chem. 1999; 2: 2183

16a Gupta RK, George MV. Tetrahedron 1975; 31: 1263
16b Yavari I, Ramazani A. Synth. Commun. 1997; 27: 1385
16c Ramaiah D, Scaria PM, Cyr DR, Das PK, George MV. J. Org. Chem. 1988; 53: 2016
16d Noshiranzadeh N, Ramazani A. Synth. Commun. 2007; 37: 3181
16e Nixon NS, Scheinmann F. Tetrahedron Lett. 1983; 24: 597
16f Shi M, Dai L.-Z, Shi Y.-L, Zhao G.-L. Adv. Synth. Catal. 2006; 348: 967

17 Maniukiewicz W, Bukowska-Strzyżewska M. Acta Crystallogr., Sect. C. 1992; C48: 1324
18 Dicken CM, DeShong P. J. Org. Chem. 1982; 47: 2047
19 Creary X. Org. Synth. Coll. Vol. VII . John Wiley & Sons; London: 1990: 438

Orthoamides and Iminium Salts LXXVII.[ 1 ] Cycloadditions to N,N,N′,N′,N′′,N′′,N′′′,N′′′-Octamethylacetylenedicarboxamidinium Bis(tetrafluoroborate): A New Synthetic Method for the Preparation of Heterocyclic Dicarboxamidinium Salts

Orthoamides and Iminium Salts LXXVII.^{[
¹
]} Cycloadditions to N,N,N′,N′,N′′,N′′,N′′′,N′′′-Octamethylacetylenedicarboxamidinium Bis(tetrafluoroborate): A New Synthetic Method for the Preparation of Heterocyclic Dicarboxamidinium Salts