Tetrazo[1,2-b]indazoles: Straightforward Access to Nitrogen-Rich Polyaromatics from s-Tetrazines.
Chromophores
Palladium
Redox Properties
Tetrazines
Tetrazo[1,2-b]Indazoles
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
20 Mar 2023
20 Mar 2023
Historique:
received:
12
01
2023
pubmed:
30
1
2023
medline:
30
1
2023
entrez:
29
1
2023
Statut:
ppublish
Résumé
The straightforward access to a new class of aza-polyaromatics is reported. Starting from readily available fluorinated s-tetrazine, a cyclization process with azide leads to the formation of an unprecedented tetrazo[1,2-b]indazole or a bis-tetrazo[1,2-b]indazole (cis and trans conformers). Based on the new nitrogen core, further N-directed palladium-catalyzed ortho-C-H bond functionalization allows the introduction of halides or acetates. The physicochemical properties of these compounds were studied by a joint experimental/theoretical approach. The tetrazo[1,2-b]indazoles display solid-state π-stacking, low reduction potential, absorption in the visible range up to the near-infrared, and intense fluorescence, depending on the molecular structure.
Identifiants
pubmed: 36710261
doi: 10.1002/anie.202300571
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300571Subventions
Organisme : Agence Nationale de la Recherche
ID : ANR-18-CE07-0015
Organisme : Agence Nationale de la Recherche
ID : ANR-21-CE07-0024-01
Organisme : Grand Équipement National De Calcul Intensif
ID : Grant 2017-A0030807259
Organisme : ISITE-BFC
ID : ISITE UB180013.MUB.IS
Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
S. M. Draper, D. J. Gregg, E. R. Schofield, W. R. Browne, M. Duati, J. G. Vos, P. Passaniti, J. Am. Chem. Soc. 2004, 126, 8694;
D. Reger, K. Schöll, F. Hampel, H. Maid, N. Jux, Chem. Eur. J. 2021, 27, 1984.
See for instance:
K. Namba, A. Osawa, S. Ishizaka, N. Kitamura, K. Tanino, J. Am. Chem. Soc. 2011, 133, 11466;
D. Sirbu, J. Diharce, I. Martinic, N. Chopin, S. V. Eliseeva, G. Guillaumet, S. Petoud, P. Bonnet, F. Suzenet, Chem. Commun. 2019, 55, 7776;
M. Daniel, M. A. Hiebel, G. Guillaumet, E. Pasquinet, F. Suzenet, Chem. Eur. J. 2020, 26, 1525.
S. Gutierrez, A. Arnault, V. Ferreira, A. Artigas, D. Hagebaum-Reignier, Y. Carissan, Y. Coquerel, M.-A. Hiebel, F. Suzenet, J. Org. Chem. 2022, 87, 13653.
G. Clavier, P. Audebert, Chem. Rev. 2010, 110, 3299;
H. Wu, N. K. Devaraj, Acc. Chem. Res. 2018, 51, 1249;
P. Audebert, F. Miomandre, Chem. Sci. 2013, 4, 575.
P. Audebert, E. Kroke, C. Posern, S. H. Lee, Chem. Rev. 2021, 121, 2515.
K. Schwärzer, S. K. Rout, D. Bessinger, F. Lima, C. E. Brocklehurst, K. Karaghiosoff, T. Bein, P. Knochel, Chem. Sci. 2021, 12, 12993;
E. Yen-Pon, P. A. Champagne, L. Plougastel, S. Gabillet, P. Thuéry, M. Johnson, G. Muller, G. Pieters, F. Taran, K. N. Houk, D. Audisio, J. Am. Chem. Soc. 2019, 141, 1435;
R. Heckerschoff, S. Maier, T. Wurm, P. Biegger, K. Bröder, P. Krämer, M. T. Hoffmann, L. Eberle, J. Stein, F. Rominger, M. Rudolph, J. Freundenberg, A. Dreuw, A. S. K. Hashmi, U. H. F. Bunz, Chem. Eur. J. 2022, 28, e202104203;
A. Suleymanov, A. Ruggi, O. Planes, A. S. Chauvin, R. Scopelliti, F. Fadaei Tirani, A. Sienkiewicz, A. Fabrizio, C. Corminboeuf, K. Severin, Chem. Eur. J. 2019, 25, 6718;
P. Karak, C. Dutta, T. Dutta, A. L. Koner, J. Choudhury, Chem. Commun. 2019, 55, 6791.
G. Soderberg, Curr. Org. Chem. 2000, 4, 727;
F. Xie, X. Li, Angew. Chem. Int. Ed. 2013, 52, 11862;
Angew. Chem. 2013, 125, 12078;
Q.-Z. Zheng, P. Feng, Y.-F. Liang, N. Jiao, Org. Lett. 2013, 15, 4262.
For pyrido[1,2-b]indazole synthesis, see:
P. Tapolcsányi, G. Krajsovszky, R. Ando, P. Lipcsey, G. Horvath, P. Matyus, Z. Riedl, G. Hajos, B. U. W. Maes, G. L. F. Lemiere, Tetrahedron 2002, 58, 10137;
R. A. Abramovitch, J. Kalinowski, Heterocycl. Chem. 1974, 857;
M. V. Méndez, S. O. Simonetti, T. S. Kaufman, A. B. Bracca, New J. Chem. 2019, 43, 10803;
J. Balog, Z. Riedl, G. Hajós, Tetrahedron Lett. 2013, 54, 5338;
D. Limbach, M. Geffe, H. Detert, ChemistrySelect 2018, 3, 249-252;
T. V. Nykaza, T. S. Harrison, A. Ghosh, R. A. Putnik, A. T. Radosevich, J. Am. Chem. Soc. 2017, 139, 6839.
C. Testa, E. Gigot, S. Genc, R. Decreau, J. Roger, J.-C. Hierso, Angew. Chem. Int. Ed. 2016, 55, 5555;
Angew. Chem. 2016, 128, 5645;
C. D. Mboyi, C. Testa, S. Reeb, S. Genc, H. Cattey, P. Fleurat-Lessard, J. Roger, J.-C. Hierso, ACS Catal. 2017, 7, 8493;
C. D. Mboyi, A. Daher, N. Khirzada, C. H. Devillers, H. Cattey, P. Fleurat-Lessard, J. Roger, J.-C. Hierso, New J. Chem. 2020, 44, 15235;
H. Xiong, Y. Gu, S. Zhang, F. Lu, Q. Ji, L. Liu, P. Ma, G. Yang, W. Hou, H. Xu, Chem. Commun. 2020, 56, 4692;
C. D. Mboyi, D. Vivier, A. Daher, P. Fleurat-Lessard, H. Cattey, C. H. Devillers, C. Bernhard, F. Denat, J. Roger, J.-C. Hierso, Angew. Chem. Int. Ed. 2020, 59, 1149;
Angew. Chem. 2020, 132, 1165.
Deposition numbers 2234376. (2 b), 2234376. (3-cis), and 2234377 (2 d) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
B. J. Stokes, C. V. Vogel, L. K. Urnezis, M. Pan, T. G. Driver, Org. Lett. 2010, 12, 2884.
Y. F. Yang, Y. Liang, F. Liu, K. N. Houk, J. Am. Chem. Soc. 2016, 138, 1660;
A. V. Polezhaev, D. M. Beagan, A. C. Cabelof, C. H. Chen, K. G. A. Caulton, Dalton Trans. 2018, 47, 5938.
R. A. Abramovitch, K. A. H. Adams, Can. J. Chem. 1961, 39, 2516.
B. J. Stokes, K. J. Richert, T. G. Driver, J. Org. Chem. 2009, 74, 6442.
Note that 3-trans is a mesoionic derivative, with electronic structure reminiscent of the azapentalene skeleton (see Figure S-Th-9). See also ref. [2].
Y.-H. Gong, F. Miomandre, R. Méallet-Renault, S. Badré, L. Galmiche, J. Tang, P. Audebert, G. Clavier, Eur. J. Org. Chem. 2009, 6121.
For solubility reasons, the comparison of spectroscopic and redox properties between 3-cis and 3-trans was made in DMSO or DMF. Note that the reversibility of the redox processes is lower in DMSO compared to DCM, see the ESI.
H. Fischer, T. Müller, I. Umminger, F. A. Neugebauer, H. Chandra, M. C. R. Symons, J. Chem. Soc. Perkin Trans. 2 1988, 413.