RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2016; 48(21): 3743-3752
DOI: 10.1055/s-0035-1561657
DOI: 10.1055/s-0035-1561657
paper
An Efficient Synthesis of 1,3-Benzothiadiazin-4(3H)-one 2-Oxides: Novel Anthranilic Acid Derivatives
Weitere Informationen
Publikationsverlauf
Received: 05. April 2016
Accepted after revision: 02. Mai 2016
Publikationsdatum:
15. Juni 2016 (online)
Abstract
Derivatives of anthranilic acid exhibit a range of useful biological activities. Herein we describe an efficient synthetic route to 1,3-benzothiadiazin-4(3H)-one 2-oxides via copper-catalyzed N-arylation of sulfonimidamides followed by cyclization. Such 1,3-benzothiadiazin-4(3H)-one 2-oxides can be viewed as novel anthranilic acid derivatives.
Key words
1,3-benzothiadiazin-4(3H)-one 2-oxides - anthranilic acid - N-arylation - sulfur - cyclization - copper catalysisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561657.
- Supporting Information
-
References
- 1a Levchenko ES, Sheinkman IE, Kirsanov AV. Zh. Obshch. Khim. 1960; 30: 1941 ; Chem. Abstr. 1961, 55, 6426
- 1b Levchenko ES, Derkach NY, Kirsanov AV. Zh. Obshch. Khim. 1962; 32: 1208 ; Chem. Abstr. 1963, 58, 1388
- 2a Johnson CR, Lavergne OM. J. Org. Chem. 1993; 58: 1922
- 2b Azzaro S, Fensterbank L, Lacôte E, Malacria M. Synlett 2008; 2253
- 2c Azzaro S, Desage-El Murr M, Fensterbank L, Lacôte E, Malacria M. Synlett 2011; 849
- 2d Maldonado MF, Sehgelmeble F, Bjarnemark F, Svensson M, Åhman J, Arvidsson PI. Tetrahedron 2012; 68: 7456
- 2e Worch C, Bolm C. Synthesis 2008; 739
- 2f Borhade SR, Sandstörm A, Arvidsson PI. Org. Lett. 2013; 15: 1056
- 2g Leca D, Toussaint A, Mareau C, Fensterbank L, Lacôte E, Malacria M. Org. Lett. 2004; 6: 3573
- 2h Rashatasakhon P, Harmata M. Chemtracts: Org. Chem. 2006; 19: 143
- 2i Di Chenna PH, Robert-Peillard F, Dauban P, Dodd RH. Org. Lett. 2004; 6: 4503
- 2j Robert-Peillard F, Di Pablo C, Liang HC, Lescot C, Collet F, Dodd RH, Dauban P. Tetrahedron: Asymmetry 2010; 21: 1447
- 2k Liang C, Robert-Peillard F, Fruit C, Mueller P, Dodd RH, Dauban P. Angew. Chem. Int. Ed. 2006; 45: 464
- 2l Lescot C, Darses B, Collet F, Retailleau P, Dauban P. J. Org. Chem. 2012; 77: 7232
- 2m Worch C, Bolm C. Synlett 2009; 2425
- 2n Steurer M, Bolm C. J. Org. Chem. 2010; 75: 3301
- 2o Patureau FW, Worch C, Siegler MA, Spek AL, Bolm C, Reek JN. H. Adv. Synth. Catal. 2012; 354: 59
- 3 Hillemann CL. EP 0173498, 1986
- 4a Paulini R, Breuninger D, von Deyn W, Bastiaans HM. M, Beyer C, Anspaugh DD, Oloumi-Sadeghi H. WO 2009156336, 2009 ; Chem. Abstr. 2009, 152, 97451
- 4b Paulini R, von Deyn W, Bastiaans HM. M, Beyer C. WO 2011069955, 2011 ; Chem. Abstr. 2011, 155, 93714
- 4c Gnamm C, Jeanguenat A, Dutton AC, Grimm C, Kloer D, Crossthwaite AJ. Bioorg. Med. Chem. Lett. 2012; 22: 3800
- 5 Cathers BE, Schloss JV. Bioorg. Med. Chem. Lett. 1999; 9: 1527
- 6 Sehgelmeble F, Janson J, Ray C, Rosqvist S, Gustavsson S, Nilsson LI, Minidis A, Holenz J, Rotticci D, Lundkvist J, Arvidsson PI. ChemMedChem 2012; 7: 396
- 7 Pemberton N, Garden H, Evertsson E, Bratt E, Lepisto M, Johannesson P, Svensson PH. ACS Med. Chem. Lett. 2012; 3: 574
- 8 Borhade SR, Svensson R, Brandt P, Artursson P, Arvidsson PI, Sandström A. ChemMedChem 2015; 10: 455
- 9 Sen I, Kloer DP, Hall RG, Pal S. Synthesis 2013; 45: 3018
- 10a Bohmann RK, Unoh Y, Miura M, Bolm C. Chem. Eur. J. 2016; 22 in press; DOI: 10.1002/chem.201600725
- 10b Walter R, Roland P. Chem. Ber. 1984; 117: 2779
- 11a Lahm GP, Selby TP, Freudenberger JH, Stevenson TM, Myers BJ, Seburyamo G, Smith BK, Flexner L, Clark CE, Cordova D. Bioorg. Med. Chem. Lett. 2005; 15: 4898
- 11b Lahm GP, Stevenson TM, Selby TP, Freudenberger JH, Cordover D, Flexner L, Bellin CA, Dubas CM, Smith BK, Hughes KA, Hollingshaus JG, Clark CE, Benner EA. Bioorg. Med. Chem. Lett. 2007; 17: 6274
- 11c Cordova D, Benner EA, Sacher MD, Rauh JJ, Sopa JS, Lahm GP, Selby TP, Stevenson TM, Flexner L, Gutteridge S, Rhoades DF, Wu L, Smith RM, Tao Y. Pestic. Biochem. Physiol. 2006; 84: 196
- 12 Bereznak JF, Chang Z.-Y, Selby TP, Sternberg CG. WO 9426722, 1994
- 13 Zeidler A, Koenig K.-H, Fischer A, Jung J. US 3621017, 1971
- 14a Johnson CR, Wambsgans A. J. Org. Chem. 1979; 44: 2278
- 14b Johnson CR, Jonsson EU, Wambsgans A. J. Org. Chem. 1979; 44: 2061
- 14c Johnson CR, Jonsson EU, Bacon CC. J. Org. Chem. 1979; 44: 2055
- 14d Okuma K, Koike T, Ohta H. J. Org. Chem. 1988; 53: 4190
- 14e Okuma K, Higuchi N, Kaji S, Takeuchi H, Ohta H, Matsuyama H, Kamigata N, Kobyashi M. Bull. Chem. Soc. Jpn. 1990; 63: 3223
- 14f Tsushima S, Yamada Y, Onami T, Oshima K, Chaney MO, Jones ND, Swartzendruber JK. Bull. Chem. Soc. Jpn. 1989; 62: 1167
- 14g Worch C, Atodiresei I, Raabe G, Bolm C. Chem. Eur. J. 2010; 16: 677
- 14h Mancheño OG, Bolm C. Beilstein J. Org. Chem. 2007; 3: 25
- 14i Pennington RL, Shab X, King SB. Bioorg. Med. Chem. Lett. 2005; 15: 2331
- 14j Levchenko ES, Markovskii LN, Shermolovich YG. Russ. J. Org. Chem. 2000; 36: 143
- 15 Johnson CR, Bis KG, Cantillo JH, Meanwell NA, Reinhard MF. D, Zeller JR, Vonk GP. J. Org. Chem. 1983; 48: 1
- 16a Battula SR. K, Subbareddy GV, Chakravarthy IE. Tetrahedron Lett. 2014; 55: 517
- 16b Nandi GC, Kota SR, Govender T, Kruger HG, Arvidsson PI. Tetrahedron 2014; 70: 5428
- 17a Paine J, Couture C. Can. J. Chem. 1985; 63: 111
- 17b Zeng L, Fu H, Qiao R, Jiang Y, Zhao Y. Adv. Synth. Catal. 2009; 351: 1671
- 18 Although drawn as structures 7 and 8p, tautomeric forms are possible and we did not assign the exact position of the NH proton.
- 19 Mintz MJ, Walling C. Org. Synth. Coll. Vol. V . John Wiley & Sons; London: 1973: 184
- 20 Scarborough RM, Jantzen H.-M, Huang W, Sedlock DM, Marlowe CK, Kane-Maguire KA. US 20020077486, 2002