[2+2] Photodimerization of Stilbazoles Promoted by Oxalic Acid in Suspension.

cyclobutane solid-state photodimerization stilbazole synthetic methods

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)

ISSN: 1521-3765

Titre abrégé: Chemistry

Pays: Germany

ID NLM: 9513783

Informations de publication

Date de publication:
09 Apr 2020

Historique:

received: 11 12 2019

pubmed: 17 1 2020

medline: 17 1 2020

entrez: 17 1 2020

Statut: ppublish

Résumé

In this study, a very simple technique to perform efficiently photodimerization of some vinylpyridines is reported. By irradiating a stirred mixture of several stilbazoles with solid oxalic acid dihydrate dispersed in a nonpolar (i.e., cyclohexane) or moderately polar (benzene, dichloromethane, dioxane) solvent, the corresponding dimeric cyclobutane adducts were obtained in high yields and excellent regio- and stereoselectivities. The strategy could also be applied successfully to oily, waxy, or even insoluble stilbazoles. Moreover, the oxalic acid loading could be lowered to substoichiometric amounts. When further optimizations were needed, our strategy was found to be highly flexible to identify other oligocarboxylic acids as alternative additives to improve, or even overturn, the regioselectivity. Oxalic acid and other oligocarboxylic acids were found to be capable of orienting more than 50 stilbazoles toward photodimerization under these conditions.

Identifiants

DOI: 10.1002/chem.201905597 PMID: 31944449

pubmed: 31944449

doi: 10.1002/chem.201905597

doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

Pagination

4682-4689

Subventions

Organisme : 2017 PHC Merlion Grant

Informations de copyright

Références

J. Vansant, S. Toppet, G. Smets, J. P. Declercq, G. Germain, M. Van Meerssche, J. Org. Chem. 1980, 45, 1565.

M. D. Cohen, G. M. J. Schmidt, F. I. Sonntag, J. Chem. Soc. 1964, 27, 2000;

G. M. J. Schmidt, Pure Appl. Chem. 1971, 27, 647;

V. Ramamurthy, K. Venkatesan, Chem. Rev. 1987, 87, 433.

L. R. MacGillivray, G. S. Papaefstathiou, T. Friscic, T. D. Hamilton, D. K. Bucar, Q. Chu, D. B. Varshney, I. G. Georgiev, Acc. Chem. Res. 2008, 41, 280;

K. Biradha, R. Santra, Chem. Soc. Rev. 2013, 42, 950.

B. R. Bhogala, B. Captain, A. Parthasarathy, V. Ramamurthy, J. Am. Chem. Soc. 2010, 132, 13434;

M. Linares, A. Briceno, New J. Chem. 2010, 34, 587;

A. L. Grobelny, N. P. Rath, R. H. Groeneman, Photochem. Photobiol. Sci. 2019, 18, 989;

G. Campillo-Alvarado, A. D. Brannan, D. C. Swenson, L. R. MacGillivray, Org. Lett. 2018, 20, 5490;

K. Tsaggeos, N. Masiera, A. Niwicka, V. Dokorou, M. G. Siskos, S. Skoulika, A. Michaelides, Cryst. Growth Des. 2012, 12, 2187;

A. Garai, K. Biradha, Cryst. Growth Des. 2019, 19, 4602;

S. Bhattacharya, J. Stojakovic, B. K. Saha, L. R. MacGillivray, Org. Lett. 2013, 15, 744;

G. Ortega, J. Hernandez, T. Gonzalez, R. Dorta, A. Briceno, Photochem. Photobiol. Sci. 2018, 17, 670;

M. Gan, J. Yu, Y. Wang, Y. Han, Cryst. Growth Des. 2018, 18, 553;

C. M. Santana, E. W. Reinheimer, Jr., H. R. Krueger, L. R. MacGillivray, R. H. Groeneman, Cryst. Growth Des. 2017, 17, 2054;

M. A. Sinnwell, J. N. Blad, L. R. Thomas, L. R. MacGillivray, IUCrJ 2018, 5, 491;

A. L. Grobelny, F. A. Verdu, R. H. Groeneman, CrystEngComm 2017, 19, 3562;

L. G. Kuz'mina, A. I. Vedernikov, J. A. K. Howard, E. K. Lermontova, A. V. Churakov, M. V. Alfimov, S. P. Gromov, J. Struct. Chem. 2014, 55, 1484;

K. M. Hutchins, J. C. Sumrak, D. C. Swenson, L. R. MacGillivray, CrystEngComm 2014, 16, 5762;

E. Elacqua, P. Kaushik, R. H. Groeneman, J. C. Sumrak, D. Bucar, L. R. MacGillivray, Angew. Chem. Int. Ed. 2012, 51, 1037;

Angew. Chem. 2012, 124, 1061.

Photoactive co-crystals between some stilbazoles and fumaric or maleic acid was described to be possible in methanol. The yields of the corresponding [2+2] photocycloaddition was shown to be enhanced by grinding assistance in the presence of the solvent prior to the irradiation: A. Briceno, D. Leal, G. Ortega, G. Dıaz de Delgado, E. Ocandoa, L. Cubillana, CrystEngComm 2013, 15, 2795.

F. L. Hu, Y. Mi, C. Zhu, B. F. Abrahams, P. Braunstein, J. P. Lang, Angew. Chem. Int. Ed. 2018, 57, 12696;

Angew. Chem. 2018, 130, 12878;

Z. Ma, S. Yang, L. Zheng, B. K. Teo, Cryst. Growth Des. 2019, 19, 3113;

M.-F. Wang, Y. Mi, F.-L. Hu, Z. Niu, X. H. Yin, Q. Huang, H.-F. Wang, J.-P. Lang, J. Am. Chem. Soc. 2020, 142, 700-704;

X. X. Shi, W. H. Zhang, B. F. Abrahams, P. Braunstein, J. P. Lang, Angew. Chem. Int. Ed. 2019, 58, 9453;

Angew. Chem. 2019, 131, 9553;

D. Liu, Z. G. Ren, H. X. Li, J. P. Lang, N. Y. Li, B. F. Abrahams, Angew. Chem. Int. Ed. 2010, 49, 4767;

Angew. Chem. 2010, 122, 4877;

F. L. Hu, H. F. Wang, D. Guo, H. Zhang, J. P. Lang, J. E. Beves, Chem. Commun. 2016, 52, 7990;

N. Y. Li, D. Liu, Z. G. Ren, C. Lollar, J. P. Lang, H. C. Zhou, Inorg. Chem. 2018, 57, 849.

D. Liu, J. Lang, CrystEngComm 2014, 16, 76;

J. H. Lee, S. Park, S. Jeoung, H. R. Moon, CrystEngComm 2017, 19, 3719;

F. Hu, S. Wang, B. F. Abrahams, J. Lang, CrystEngComm 2015, 17, 4903;

R. Medishetty, Z. Bai, H. Yang, M. W. Wong, J. J. Vittal, Cryst. Growth Des. 2015, 15, 4055;

R. Medishetty, R. Tandiana, J. Wu, Z. Bai, Y. Du, J. J. Vittal, Chem. Eur. J. 2015, 21, 11948;

R. Medishetty, A. Husain, Z. Bai, T. Runcevski, R. E. Dinnebier, P. Naumov, J. J. Vittal, Angew. Chem. Int. Ed. 2014, 53, 5907;

Angew. Chem. 2014, 126, 6017;

R. Medishetty, T. T. S. Yap, L. L. Koh, J. J. Vittal, Chem. Commun. 2013, 49, 9567;

R. Medishetty, L. L. Koh, G. K. Kole, J. J. Vittal, Angew. Chem. Int. Ed. 2011, 50, 10949;

Angew. Chem. 2011, 123, 11141;

K. Yadava, J. J. Vittal, Chem. Eur. J. 2019, 25, 10394;

J. Chen, Y. Hou, Q. Zhou, H. Zhang, D. Liu, CrystEngComm 2017, 19, 2603;

G. Li, W. Yin, G. Liu, L. Ma, L. Huang, L. Li, L. Wang, Inorg. Chem. Commun. 2014, 43, 165;

D. Liu, J. Lang, B. F. Abrahams, Chem. Commun. 2013, 49, 2682.

S. Yamada, N. Uematsu, K. Yamashita, J. Am. Chem. Soc. 2007, 129, 12100;

S. Yamada, Y. Nojiri, Chem. Commun. 2011, 47, 9143;

B. Mondal, T. Zhang, R. Prabhakar, B. Captain, V. Ramamurthy, Photochem. Photobiol. Sci. 2014, 13, 1509;

L. G. Kuz'mina, A. I. Vedernikov, S. K. Sazonov, N. A. Lobova, A. V. Churakov, E. K. Lermontova, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, Russian Chem. Bull. 2011, 60, 1734;

S. Yamada, Y. Nojiri, M. Sugawara, Tetrahedron Lett. 2010, 51, 2533;

X. Li, L. Wu, L. Zhang, C. Tung, Org. Lett. 2002, 4, 1175;

K. Takagi, H. Usami, T. Shiichi, Y. Sawaki, Mol. Cryst. Liq. Cryst. 1992, 218, 109;

H. Usami, K. Takagi, Y. Sawaki, J. Chem. Soc. Perkin Trans. 2 1990, 10, 1723;

K. Takagi, B. R. Suddaby, S. L. Vadas, C. A. Backer, D. G. Whitten, J. Am. Chem. Soc. 1986, 108, 7865;

M. Horner, S. Hünig, Liebigs Ann. Chem. 1982, 1183;

F. H. Quina, D. G. Whitten, J. Am. Chem. Soc. 1977, 99, 877;

F. H. Quina, D. G. Whitten, J. Am. Chem. Soc. 1975, 97, 1602;

G. K. Kole, U. Sambasivam, G. K. Tan, J. J. Vittal, Cryst. Growth Des. 2017, 17, 2694;

S. Yamada, N. Sako, K. Yamada, K. Deguchi, T. Shimizu, CrystEngComm 2015, 17, 5629;

S. Yamada, Y. Nojiri, S. Fukuzumi, Molecules 2017, 22, 491.

A. Nakamura, H. Irie, S. Hara, M. Sugawara, S. Yamada, Photochem. Photobiol. Sci. 2011, 10, 1496.

D. V. Berdnikova, T. M. Aliyeu, S. Delbaere, Y. V. Fedorov, G. Jonusauskas, V. V. Novikov, A. A. Pavlov, A. S. Peregudov, N. E. Shepel, F. I. Zubkov, O. A. Fedorova, Dyes Pigm. 2017, 139, 397;

L. G. Kuz′mina, A. I. Vedernikov, A. V. Churakov, E. K. Lermontova, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, CrystEngComm 2014, 16, 5364.

For selected reviews on cyclobutane natural products, see:

M. A. Beniddir, L. Evanno, D. Joseph, A. Skiredj, E. Poupon, Nat. Prod. Rep. 2016, 33, 820;

A. Sergeiko, V. V. Poroikov, L. O. Hanuš, V. M. Dembitsky, Open Med. Chem. J. 2008, 2, 26.

T. B. Nguyen, A. Almourabit, Photochem. Photobiol. Sci. 2016, 15, 1115.

The reactions were performed in a 7-mL Pyrex tube containing 0.1 mmol olefin in 2 mL dispersing solvent. The reaction tubes were magnetically stirred and exposed to 365 nm UV light generated by 20 PL-L 36W/10/4P Philips bulb tubes in a reflective box cooled by an electric fan (35 °C). For more details on the reaction setup, see the Supporting Information.

The insolubility of these carboxylic acid additives were readily observed by gravimetric analysis or by 1H NMR investigation on their saturated solution in cyclohexane-d12.

Please compare this result with the formation of α17 adduct according to a previous report (Ref. [4h]) emphasizing the importance of using 1,2,3,4-benzenetetracarboxylic acid as the hydrogen-bonding template. Ref. [4a] described the use of thiourea as a template to orient olefin A17 to provide β-truxinic-acid-type adduct β17.

This compound was previously obtained by irradiating a toluene solution of the parent stilbazole A30 under air.

N. Tateda, K. Matsuhisa, K. Hasebe, T. Miura, Anal. Sci. 2001, 17, 775;

P. McLoone, E. Simics, A. Barton, M. Norval, N. Gibbs, J. Invest. Dermatol. 2005, 124, 1071;

N. K. Gibbs, J. Tye, M. Norval, Photochem. Photobiol. Sci. 2008, 7, 655;

N. K. Gibbs, M. Norval, J. Invest. Dermatol. 2011, 131, 14.

Urocanic acid as a salt formed with hydrochloric acid or potassium hydroxide in aqueous solution was found to undergo [2+2] photodimerization: J. J. H. Anglin, W. H. Batten, Photochem. Photobiol. 1970, 11, 271.

M. D'Auria, R. Raicoppi, Photochem. Photobiol. 1998, 112, 145;

S. Ohta, A. Khadeer, A. Kakuno, I. Kawasaki, M. Yamashita, Heterocycles 2007, 71, 815;

D. P. O'Malley, K. Li, M. Maue, A. L. Zografos, P. S. Baran, J. Am. Chem. Soc. 2007, 129, 4762.

Urocanic was found to undergo cross [2+2] cycloaddition with thymidine in solution: S. J. Farrow, C. R. Jones, D. L. Severance, R. M. Deibel, W. M. Baird, H. A. Morrison, J. Org. Chem. 1990, 55, 275.

T. B. Nguyen, L. A. Nguyen, M. Corbin, P. Retailleau, L. Ermolenko, A. Almourabit, Eur. J. Org. Chem. 2018, 5861.