Synthesis 2023; 55(20): 3263-3271 DOI: 10.1055/a-2086-3015
Synthesis of Trifunctional Thiazole-Fused Anthranilonitrile and Anthranilic Acid Derivatives
,
Alexandra Pacheco-Benichou
,
,
This work was partially supported by the Université de Rouen Normandie (University of Rouen Normandy), the Institut National des Sciences Appliquées Rouen Normandie (INSA Rouen Normandy), the Centre National de la Recherche Scientifique (CNRS), the European Regional Development Fund (ERDF), Labex SynOrg (ANR-11-LABX-0029), Institut Carnot I2C, and the XL-Chem Graduate School of Research (ANR-18-EURE-0020 XL CHEM). N.B. and A.P.-B. thank the Ministère de l’Enseignement Supérieur, de la Recherche et de l’Innovation (MESRI) and Région Normandie for Ph.D. grants.
Abstract
The synthesis of trifunctional isomeric benzothiazoles derived from nitroanthranilic acids and their corresponding anthranilonitrile analogues is studied. Compared to previous work, the reaction sequence affords convenient access to hitherto undescribed 2-cyanobenzothiazoles. For further synthetic applications of these polyfunctional compounds, a hydrolysis–decarboxylation sequence is performed in an acidic medium (HCl or HBr), leading to an enlarged array of relevant building blocks.
Key words
N -arylcyanothioformamides -
4,5-dichloro-1,2,3-dithiazolium chloride -
N -arylimino-1,2,3-dithiazoles -
2-cyanobenzothiazoles -
anthranilic acid -
anthranilonitrile -
intramolecular C–S bond formation -
decyanation
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/a-2086-3015.
Supporting Information
Publication History
Received: 31 March 2023
Accepted after revision: 04 May 2023
Accepted Manuscript online: 04 May 2023
Article published online: 01 June 2023
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References
1a
Beauchard A,
Jaunet A,
Murillo L,
Baldeyrou B,
Lansiaux A,
Chérouvrier JR,
Domon L,
Picot L,
Bailly C,
Besson T,
Thiéry V.
Eur. J. Med. Chem. 2009; 44: 3858
1b
Guillon R,
Pagniez F,
Picot C,
Hédou D,
Tonnerre A,
Chosson E,
Duflos M,
Besson T,
Logé C,
Le Pape P.
ACS Med. Chem. Lett. 2013; 4: 288
1c
Foucourt A,
Hédou D,
Dubouilh-Benard C,
Girard A,
Taverne T,
Casagrande A.-S,
Désiré L,
Leblond B,
Besson T.
Molecules 2014; 19: 15411
1d
Foucourt A,
Hédou D,
Dubouilh-Benard C,
Girard A,
Taverne T,
Désiré L,
Casagrande A.-S,
Leblond B,
Loaëc N,
Meijer L,
Besson T.
Molecules 2014; 19: 15546
For relevant reviews, see:
2a
Le Bozec L,
Moody CJ.
Aust. J. Chem. 2009; 62: 639
2b
Noolvi MN,
Patel HM,
Kaur M.
Eur. J. Med. Chem. 2012; 54: 447
2c
Kamal A,
Syed MA. H,
Mohammed SM.
Expert Opin. Ther. Pat. 2015; 25: 335
2d
Keri RS,
Patil MR,
Patil SA,
Budagumpi SA.
Eur. J. Med. Chem. 2015; 89: 207
2e
Irfan A,
Batool F,
Naqvi SA. Z,
Islam A,
Osman SM,
Nocentini A,
Alissa SA,
Supuran CT.
J. Enzym. Inhib. Med. Chem. 2020; 35: 265
2f
Law CS. W,
Yeong KY.
Expert Opin. Ther. Pat. 2022; 32: 299
2g
Qadir T,
Amin A,
Salhotra A,
Sharma PK,
Jeelani I,
Abe H.
Curr. Org. Chem. 2022; 26: 189
3
Hédou D,
Deau E,
Harari M,
Sanselme M,
Fruit C,
Besson T.
Tetrahedron 2014; 70: 5541
4
Hédou D,
Harari M,
Godeau J,
Dubouilh-Benard C,
Fruit C,
Besson T.
Tetrahedron Lett. 2015; 56: 4088
5
Hédou D,
Godeau J,
Loaëc N,
Meijer L,
Fruit C,
Besson T.
Molecules 2016; 21: 578
6a
Appel R,
Janssen H,
Siray M,
Knoch F.
Chem. Ber. 1985; 118: 1632
6b
Rees CW.
J. Heterocycl. Chem. 1992; 29: 639
7
Godeau J,
Martinet A,
Levacher V,
Fruit C,
Besson T.
Synthesis 2016; 48: 3504
8
Broudic N,
Pacheco-Benichou A,
Fruit C,
Besson T.
Molecules 2022; 27: 8426
9 Michaelidou S. S.; Koutentis P. A. Synthesis
2009 , 4167.
10a
El-Sharief AM. Sh,
Moussa Z.
Eur. J. Med. Chem. 2009; 44: 4315
10b
Moussa Z,
Judeh ZM. A,
El-Sharief MA. M. Sh,
El-Sharief AM. Sh.
ChemistrySelect 2020; 5: 764
11
Besson T,
Guillard J,
Rees CW,
Thiéry V.
J. Chem. Soc., Perkin Trans. 1 1998; 889
12a
Harari M,
Couly F,
Fruit C,
Besson T.
Org. Lett. 2016; 18: 3282
12b
Couly F,
Dubouilh-Benard C,
Besson T,
Fruit C.
Synthesis 2017; 49: 4615
12c
Pacheco-Benichou A,
Ivendengani E,
Kostakis IK,
Besson T,
Fruit C.
Catalysts 2021; 11: 28
13a
Yuan Y,
Liang G.
Org. Biomol. Chem. 2014; 12: 865
13b
Wang W,
Gao J.
J. Org. Chem. 2020; 85: 1756
13c
Williams SJ,
Hwang CS,
Prescher JA.
Biochemistry 2021; 60: 563
13d
Zhu Y,
Zhang X,
You Q,
Jiang Z.
Bioorg. Med. Chem. 2022; 68: 116881
14a
Khan I,
Ibrar A,
Abbas N,
Saeed A.
Eur. J. Med. Chem. 2014; 76: 193
14b
Prasher P,
Sharma M.
Drug Dev. Res. 2021; 82: 945