A Convenient Preparation of 9H-Carbazole-3,6-dicarbonitrile and 9H-Carbazole-3,6-dicarboxylic Acid

Łukasz J. Weseliński; Ryan Luebke; Mohamed Eddaoudi

doi:10.1055/s-0033-1340557

Synthesis, Table of Contents

Synthesis 2014; 46(05): 596-599
DOI: 10.1055/s-0033-1340557

practical synthetic procedures

A Convenient Preparation of 9H-Carbazole-3,6-dicarbonitrile and 9H-Carbazole-3,6-dicarboxylic Acid

Łukasz J. Weseliński

Functional Material Design, Discovery and Development (FMD3), Advanced Membranes and Porous Materials Center, Division of Physical Sciences and Engineering, 4700 King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia Fax: +966(2)8082778 Email: mohamed.eddaoudi@kaust.edu.sa

,

Ryan Luebke

Functional Material Design, Discovery and Development (FMD3), Advanced Membranes and Porous Materials Center, Division of Physical Sciences and Engineering, 4700 King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia Fax: +966(2)8082778 Email: mohamed.eddaoudi@kaust.edu.sa

,

Mohamed Eddaoudi*

Functional Material Design, Discovery and Development (FMD3), Advanced Membranes and Porous Materials Center, Division of Physical Sciences and Engineering, 4700 King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia Fax: +966(2)8082778 Email: mohamed.eddaoudi@kaust.edu.sa

› Author Affiliations

Abstract

All articles of this category

Abstract

A catalytic, high yielding and scalable procedure for the synthesis of 9H-carbazole-3,6-dicarbonitrile has been developed. Subsequent hydrolysis of the dinitrile in the presence of a catalytic copper species (i.e., CuI) yields 9H-carbazole-3,6-dicarboxylic acid. Both compounds are versatile and fine-tunable organic building blocks and therefore offer potential in material science, medicinal and supramolecular chemistry.

Key words

carbazoles - catalytic cyanation - heterocycles - metal–organic frameworks - palladium catalysis - supramolecular chemistry

Full Text

References

References

1a Nouar F, Eckert J, Eubank JF, Forster P, Eddaoudi M. J. Am. Chem. Soc. 2009; 131: 2864
1b Suh MP, Park HJ, Prasad TK, Lim D.-W. Chem. Rev. 2012; 112: 782
1c Nugent P, Belmabkhout Y, Burd SD, Cairns AC, Luebke R, Forrest K, Pham T, Ma S, Space B, Wojtas L, Eddaoudi M, Zaworotko MJ. Nature 2013; 495: 80
1d Li J.-R, Sculley J, Zhou H.-C. Chem. Rev. 2012; 112: 869
1e Alkordi MH, Liu Y, Larsen RW, Eubank JF, Eddaoudi M. J. Am. Chem. Soc. 2008; 130: 12639
1f Yoon M, Srirambalaji R, Kim K. Chem. Rev. 2012; 112: 1196
1g Liu Y, Kravtsov VCh, Larsen R, Eddaoudi M. Chem. Commun. 2006; 1488
1h Kreno LE, Leong K, Farha OK, Allendorf M, Van Duyne RP, Hupp JT. Chem. Rev. 2012; 112: 1105

2 Eubank JF, Nouar F, Luebke R, Cairns AJ, Wojtas L, Alkordi M, Bousquet T, Hight MR, Eckert J, Embs JP, Georgiev PA, Eddaoudi M. Angew. Chem. Int. Ed. 2012; 51: 10099

For selected recent reviews, see:

3a Knölker H.-J, Reddy KR. Chem. Rev. 2002; 102: 4303
3b Knölker H.-J. Curr. Org. Synth. 2004; 1: 309
3c Knölker H.-J, Reddy KR In The Alkaloids . Vol. 65. Cordell GA. Academic Press; Amsterdam: 2008: 1-430
3d Schmidt AW, Reddy KR, Knölker HJ. Chem. Rev. 2012; 112: 3193

For selected recent reviews, see:

4a Grazulevicius JV, Strohriegl P, Pielichowski J, Pielichowski K. Prog. Polym. Sci. 2003; 28: 1297
4b Organic Light Emitting Devices: Synthesis, Properties, and Applications. Müllen K, Scherf U. Wiley-VCH; Weinheim: 2006
4c Tao Y, Yang C, Qin J. Chem. Soc. Rev. 2011; 40: 2943

5 Li J.-R, Timmons DJ, Zhou H.-C. J. Am. Chem. Soc. 2009; 131: 6368

6a Li J.-R, Zhou H.-C. Angew. Chem. Int. Ed. 2009; 48: 8465
6b Li J.-R, Yakovenko AA, Lu W, Timmons DJ, Zhuang W, Yuan D, Zhou H.-C. J. Am. Chem. Soc. 2010; 132: 17599

7 Lu W, Yuan D, Makal TA, Li J.-R, Zhou H.-C. Angew. Chem. Int. Ed. 2012; 51: 1580
8 Stoeck U, Krause S, Bon V, Senkovska I, Kaskel S. Chem. Commun. 2012; 48: 10841
9 Lu W, Yuan D, Makal TA, Wei Z, Li J.-R, Zhou H.-C. Dalton Trans. 2013; 42: 1708
10 Tian Y.-P, Zhu Y.-M, Zhou H.-P, Wang P, Wu J.-Y, Tao X.-T, Jiang M.-H. Eur. J. Inorg. Chem. 2007; 345

11a Lonergan DG, Deslongschamps G. Tetrahedron Lett. 1998; 39: 7861
11b Xu D, Liu X, Lu R, Xue P, Zhang X, Zhou H, Jia J. Org. Biomol. Chem. 2011; 9: 1523

12a Nagai Y, Haung C.-C. Bull. Chem. Soc. Jpn. 1966; 39: 650
12b Meng H, Chen Z.-K, Liu X.-L, Lai Y.-H, Chua S.-J, Huang W. Phys. Chem. Chem. Phys. 1999; 1: 3123
12c Shi H.-p, Cheng Y, Jing W.-j, Chao J.-B, Fang L, Dong X, Dong C. Spectrochim. Acta, Part A 2010; 75: 525
12d Chen H.-F, Chi L.-C, Hung W.-Y, Chen W.-J, Hwu T.-Y, Chen Y.-H, Chou S.-H, Mondal E, Liu Y.-H, Wong K.-T. Org. Electron. 2012; 13: 2671

13 Albrecht WL, Fleming RW, Horgan SW, Mayer GD. J. Med. Chem. 1977; 20: 364
14 He C, Wang J, Zhao L, Liu T, Zhang J, Duan C. Chem. Commun. 2013; 49: 627

For selected recent reviews, see:

15a Knölker H.-J. Top. Curr. Chem. 2005; 244: 115
15b Knölker H.-J. Chem. Lett. 2009; 38: 8
15c Bauer I, Knölker H.-J. Top. Curr. Chem. 2012; 309: 203
15d Roy J, Jana AK, Mal D. Tetrahedron 2012; 68: 6099 ; and references cited therein

For selected recent examples, see:

15e Knott KE, Auschill S, Jager A, Knölker H.-J. Chem. Commun. 2009; 1467
15f Chmielewski MJ. Synthesis 2010; 3067
15g Gruner KK, Hopfmann T, Matsumoto K, Jager A, Katsuki T, Knölker H.-J. Org. Biomol. Chem. 2011; 9: 2057
15h Knölker H.-J, Fuchsenberger M, Forke R. Synlett 2011; 2056
15i Yang W, Zhou J, Wang B, Ren H. Chem. Eur. J. 2011; 17: 13665
15j Gensch T, Rönnefahrt M, Czerwonka R, Jäger A, Kataeva O, Bauer I, Knölker H.-J. Chem. Eur. J. 2012; 18: 770
15k Borger C, Kataeva O, Knölker H.-J. Org. Biomol. Chem. 2012; 10: 7269
15l Xiao F, Liao Y, Wu M, Deng G.-J. Green Chem. 2012; 14: 3277
15m Knölker H.-J, Berndt A, Gruner M, Schmidt A. Synlett 2013; 24: 2102
15n Hesse R, Gruner KK, Kataeva O, Schmidt AW, Knölker H.-J. Chem. Eur. J. 2013; 19: 14098
15o Kumar VP, Gruner KK, Kataeva O, Knölker H.-J. Angew. Chem. Int. Ed. 2013; 52: 11073
15p Jiang Q, Duan-Mu D, Zhong W, Chen H, Yan H. Chem. Eur. J. 2013; 19: 1903

16a Dunlop HG, Tucker SH. J. Chem. Soc. 1939; 1945
16b Preston WG, Tucker SH, Cameron JM. L. J. Chem. Soc. 1942; 500

17a Sprague PW. US 4061655, 1977
17b Patrick DA, Boykin DW, Wilson WD, Tanious FA, Spychala J, Bender BC, Hall JE, Dykstra CC, Ohemeng KA, Tidwell RR. Eur. J. Med. Chem. 1997; 32: 781
17c Yang Y, Xue M, Marshall LJ, de Mendoza J. Org. Lett. 2011; 13: 3186

18 Anbarasan P, Schareina T, Beller M. Chem. Soc. Rev. 2011; 40: 5049 ; and references cited therein
19 Maligres PE, Waters MS, Fleiz F, Askin D. Tetrahedron Lett. 1999; 40: 8193
20 Chidambaram R. Tetrahedron Lett. 2004; 45: 1441

21a Velasco D, Castellanos S, López M, López-Calahorra F, Brillas E, Juliá L. J. Org. Chem. 2007; 72: 7523
21b Geyer AM, Wiedner ES, Gary JB, Gdula RL, Kuhlmann NC, Johnson MJ. A, Dunietz BD, Kampf JW. J. Am. Chem. Soc. 2008; 130: 8984
21c Kinoshita M, Takamura K, Kawamoto M, Shishido A, Shiono T, Ikeda T. Mol. Cryst. Liq. Cryst. 2012; 563: 92

22a Brendle JJ, Outlaw A, Kumar A, Boykin DW, Patrick DA, Tidwell RR, Werbovetz KA. Antimicrob. Agents Chemother. 2002; 46: 797
22b MacMillan KS, Naidoo J, Liang J, Melito L, Williams NS, Morlock L, Huntington PJ, Estill SJ, Longgood J, Becker GL, McKnight SL, Pieper AA, De Brabander JK, Ready JM. J. Am. Chem. Soc. 2011; 133: 1428

23 Wei K.-J, Ni J, Gao J, Liu Y, Liu Q.-L. Eur. J. Inorg. Chem. 2007; 3868
24 Li Z, Wang L, Zhou X. Adv. Synth. Catal. 2012; 354: 584 ; and references cited therein
25 Crystallographic data for compound 3·DMF: C₁₇H₁₆N₂O₅, M = 328.32, monoclinic, space group P 1 21/C 1, a = 6.0698(6) Å, b = 15.9150(15) Å, c = 16.8083(15) Å, α = 90°, β = 108.148(5)°, γ = 90°, V = 1542.9(3) Å³, D _calcd = 1.413 g/cm³, T = 100 K, Z = 4; reflections collected/unique: 10482/6623, R(all) = 0.0483, wR(gt) = 0.1524. CCDC 938820 contains the supplementary crystallographic data for this paper. Copies of the data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
26 Mitchell DR, Plant SG. P. J. Chem. Soc. 1936; 1295