Abstract
A convenient and simple method of formylating 1H-isothiochromen-4(3H)-one 2,2-dioxide was carried out using dimethylformamide dimethylacetal. The reactions of 3-[(dimethylamino)methylene]-1H-isothiochromen-4(3H)-one 2,2-dioxide with nitrogen-containing nucleophilic reagents were investigated.
Graphical abstract
.
Similar content being viewed by others
References
Simpkins NS (1993) Sulfones in organic synthesis. Pergamon, Oxford, p 381
Peixoto C, Laurin P, Klich M, Dupuis-Hamelin C, Mauvais P, Lassaigne P, Bonnefoy A, Musicki B (2000) Tetrahedron Lett 41:1741
Pfizer Inc. (1972) Antiinflammatory isothiochroman carboxamides. GB Patent 1259415, 5 Jan 1972 (Chem Abstr 76:72408)
Toshima K, Ohta K, Ohtasuka A, Matsumura S, Nakata M (1993) J Chem Soc Chem Commun 18:1406
Sohda T, Tsuda M, Yamazaki I (1991) Sulfur-containing heterocyclic compounds useful for the treatment of osteoporosis, and their production. US Patent 5,071,841, 10 Dec 1991 (Chem Abstr 114:23804)
Ohta T, Komoriya S, Yoshino T, Uoto K, Nokomoto Y, Naito H, Mochizuki A, Nagata T, Kanno H, Haginoya N, Yoshikawa K, Nagamochi M, Kobayashi S, Ono M (2004) Diamine derivatives. EP 1,405,852, 7 Apr 2004 (Chem Abstr 138:73271)
John V, Maillard M, Fang L, Tucker J, Brogley L, Aquino J, Bowers J, Probst G, Tung J (2005) Methods of treatment of amyloidosis using bicyclic aspartyl protease inhibitors. Patent WO 2005/087714, 22 Sept 2005 (Chem Abstr 143:326226)
Zhu Q, Fang L, Zhang G (2000) Zhongguo Yaowu Huaxue Zazhi 10:1
Dey D, Neogi P, Sen A, Sharma SD, Nag B (2002) Tricyclic compounds and uses thereof. Patent WO 02/30888, 18 Apr 2002 (Chem Abstr 136:309858)
Krishna MV, Ramadas SR (1981) Heterocycles 16:405
Ramadas SR, Chenchaiah C (1981) Steroids 37:353
Terasawa T, Okada T (1979) J Chem Soc Perkin Trans 1:990
Reddy NS, Reddy EP, Reddy MVR (2004) Synth Commun 34:2691
Pulman DA, Whiting DA (1973) J Chem Soc Perkin Trans 1:410
Still IWJ, Wilson DKT (1992) Can J Chem 70:964
Shyshkina OO, Tkachuk TM, Volovnenko TA, Volovenko YM, Zubatyuk RI, Medviediev VV, Shishkin OV (2012) Tetrahedron Lett 53:4296
Sheldrick G (2008) Acta Crystallogr A 64:112
Acknowledgments
We are grateful to the Analytical Department for performing spectral analysis. Research was performed within the ISRA French-Ukrainian Association in Molecular Chemistry.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Tkachuk, T.M., Shyshkina, O.O., Volovnenko, T.A. et al. Novel transformations of 1H-isothiochromen-4(3H)-one 2,2-dioxide. Monatsh Chem 144, 263–271 (2013). https://doi.org/10.1007/s00706-012-0858-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-012-0858-6