Polycyclic Aromatic N-Heterocycles (PANHs) from Naphthyl and Anthracenyl Amines and Diols

Abstract

Nitrogen-containing polyaromatic compounds have been prepared in one step by combining diols and anthracenyl or naphthyl amines via acceptorless dehydrogenative condensation with ZnO and Pt/Al₂O₃ as heterogeneous catalysts.

Key words

acceptorless dehydrogenative condensation - amines - diols - heterocycles - heterogeneous catalysis - polyaromatics

• References

• 1 Novoselov KS, Geim AK, Morozov SV, Jiang D, Zhang Y, Dubonos SV, Grigorieva IV, Firsov AA. Science 2004; 306: 666
• 2 Geim AK, Novoselov KS. Nat. Mater. 2007; 6: 183
• 3 Geim AK. Science 2009; 324: 1530
• 4 Novoselov KS, Fal’ko VI, Colombo L, Gellert PR, Schwab MG, Kim K. Nature 2012; 490: 192
• 5 Wang XY, Yao X, Müllen K. Sci. China: Chem. 2019; 62: 1099
• 6 Wu J, Pisula W, Müllen K. Chem. Rev. 2007; 107: 718
• 7 Wang XY, Yao X, Narita A, Müllen K. Acc. Chem. Res. 2019; 52: 2491
• 8 Zhou L, Wu B, Chen Y, Gong J, Wang J, Dai G, Chi C, Wang Q. Org Lett. 2021; 21: 8640
• 9a Gunanathan C, Milstein D. Science 2013; 341: 1229712
• 9b Irrgang T, Kempe R. Chem. Rev. 2019; 119: 2524
• 9c Li H, Guo H, Fang Z, Aida TM, Smith RL. Jr. Green Chem. 2020; 22: 582
• 10a Nandakumar A, Midya SP, Landge VG, Balaraman E. Angew. Chem. Int. Ed. 2015; 54: 11022
• 10b Sun K, Shan H, Lu G.-P, Cai C, Beller M. Angew. Chem. Int. Ed. 2021; 60: 2
• 11a Ballesteros-Garrido R. Diols: Synthesis and Reactions . Ballard E. Nova Science; New York: 2020: 109
• 11b Llabres-Campaner PJ, Ballesteros-Garrido R, Ballesteros R, Abarca B. Tetrahedron 2017; 73: 5552
• 11c Llabres-Campaner PJ, Ballesteros-Garrido R, Ballesteros R, Abarca B. J. Org. Chem. 2018; 83: 521
• 12 Bellezza D, Zaragozá RJ, Aurell MJ, Ballesteros R, Ballesteros-Garrido R. Org. Biomol. Chem. 2021; 19: 677
• 13 Tsuji Y, Hub K.-T, Watanabe Y. J. Org. Chem. 1987; 52: 1673
• 14 Aramoto H, Obora Y, Ishii Y. J. Org. Chem. 2009; 74: 628
• 15 Tursky M, Lorentz-Petersen L, Olsen LB, Madsen R. Org. Biomol. Chem. 2010; 8: 5576
• 16 Liang Y, Ji J, Zhang X, Jiang Q, Zhao X. Angew. Chem. Int. Ed. 2020; 59: 4959
• 17a Smith MB, Guo LC, Okeyo S, Stenzel J, Yanella J, LaChapelle E. Org. Lett. 2002; 4: 2321
• 17b Li PG, Yang Y, Zhu S, Li H.-X, Zou L.-H. Eur. J. Org. Chem. 2019; 73
• 18a Wöhrle D, Meissner D. Adv. Mater. 1991; 3: 129
• 18b Sathiyan G, Sivakumar EK. T, Ganesamoorthy R, Thangamuthu R, Sakthivel P. Tetrahedron Lett. 2016; 57: 243
• 19a Schmidt AW, Reddy KR, Knölker H.-J. Chem. Rev. 2012; 112: 3193
• 19b Bauer I, Knölker H.-J. Top. Curr. Chem. 2012; 309: 203
• 19c Knolker H.-J. Curr. Org. Synth. 2004; 1: 309
• 20 Knolker H.-J, Reddy KR. Chem. Rev. 2002; 102: 4303
• 21 Nygaard R, Madsen R. Org. Biomol. Chem. 2011; 9: 610
• 22 Baudin JB, Julia SA, Ruel O. Tetrahedron 1987; 43: 881
• 23 Sakamoto T, Kondo Y, Yamanaka H. Heterocycles 1986; 24: 1845
• 24 Chen H, Shang H, Liu Y, Guo R, Lin W. Adv. Funct. Mater. 2016; 26: 8128
• 25 Pennington FC, Jellinex M, Thurn RD. J. Org. Chem. 1959; 24: 565
• 26 Jeong J, Leeab D, Chang S. Chem. Commun. 2015; 51: 7035
• 27 Adam R, Cabrero-Antonino JR, Spannenberg A, Junge K, Jackstell R, Beller MA. Angew. Chem. Int. Ed. 2017; 56: 3216
• 28 Tanga MJ, Almquist RG, Smith TH, Wu HY, Reist EJ. J. Heterocycl. Chem. 1985; 22: 1597