Effective Synthesis of 1,5-Disubstituted 2,1-Benzisothiazol-3(1H)-ones

REFERENCES

• (a) Davis , M. Benzisothiazoles . Adv. Heterocycl. Chem. 1972 , 14 , 43 ; (b) Pain , D. L. ; Peart , B. J. ; Wooldridge , K. R. H. In Comprehensive Heterocyclic Chemistry; A. R. Katrizky, C. W. Rees, K. T. Potts (Eds.); Pergamon: Oxford, 1984; vol. 6, p. 175.
   Google Scholar
• (a) Bao , M. ; Shimizu , M. ; Shimada , S. ; Inoue , J. ; Konakahara , T. Reactions of N-sulfenyl-1,2-benzisothiazolin-3-ones with nucleophiles . Tetrahedron 2004 , 60 , 11359 – 11366 ; (b) Shimizu , M. ; Sugano , Y. ; Konakahara , T. ; Gama , Y. ; Shibuya , I. An effective synthesis of N-substituted 2-sulfenamoylbenzoates and 1,2-benzisothiazolin-3-ones that uses 1,2-benzisothiazolin-3-one as a leaving group . Tetrahedron 2002 , 58 , 3779 – 3783 ; (c) Sano , T. ; Takagi , T. ; Gama , Y. ; Shibuya , I. ; Shimizu , M. A practical synthesis of N-substituted 1,2-benzisothiazolin-3-ones from N,N′-disubstituted 2,2′-dithiodibenzamides . Synthesis 2004 , 10 , 1585 – 1588 ; (d) Austin , P. W. N-(β-Branched alkyl)-1,2-benzisothiazolin-3-ones, their preparation and use as industrial biocides . WO Patent 1994/020479, 1994 ; Chem. Abstr. 1994 , 121 , 300882m .
   Web of Science ®Google Scholar
• (a) Davis , M. ; Hook , R. J. ; Wu , W. Y. 2,1-Benzisothiazoles, XIII: Intermediates and products in the sulfur extrusion reaction of 2,1-benzisothiazolin-3(1H)-one: A new synthesis of 11H-pyrido[2,1-b]quinazolin-11-one (pyracridone) . J. Heterocycl. Chem. 1984 , 21 , 369 – 373 ; (b) Davis , M. ; Hudson , M. J. 2,1-Benzisothiazoles, XII: The use of N-substituted-2,1-benzisothiazolium salts as synthetic equivalents of o-aminobenzaldehydes: A simple synthesis of some 2-quinolones . J. Heterocycl. Chem. 1983 , 20 , 1707 – 1708 ; (c) Davis , M. ; Pogany , S. P. 2,1-Benzisothiazoles, X: Acylation of 2,1-benzisothiazolin-3-one: A remarkable sulfur extrusion with ring expansion . J. Heterocycl. Chem. 1977 , 14 , 267 ; (d) Perronet , J. ; Taliani , L. Action des isocyanates sur les benzisothiazol-2,1 ones-3 (1H) et sur les thiadiazol-1,2,4 ones-5: un nouveau rearrangement avec extrusion de l'atome de soufre . J. Heterocycl. Chem. 1980 , 17 , 673 ; (e) Albert , A. H. ; O'Brien , D. E. ; Robins , R. K. The synthesis and reactions of certain 3-substituted-2,1-benzisothiazoles . J. Heterocycl. Chem. 1978 , 529 – 536 .
   Web of Science ®Google Scholar
• (a) Thorave , A. A. ; Prajapati , P. N. ; Pethani , J. P. ; Kothari , K. C. ; Jain , M. R. ; Patel , P. R. ; Kharul , R. K. Facile and convenient strategy towards synthesis of 4-substituted 2-aminothiazolo[4,5-d]pyridazinones . Tetrahedron Lett. 2009 , 50 , 5660 – 5663 ; (b) Kharul , R. ; Gite , A. ; Goswami , A. ; Jain , M. ; Pandey , B. ; Patel , P. Efficient synthesis of structurally novel diaryl ethers by regioselective functionalization . Synth. Commun. 2008 , 38 , 4282 – 4294 ; (c) Kharul , R. ; Goswami , A. ; Gite , A. ; Godha , A. ; Jain , M. ; Patel , P. Convenient synthesis of structurally novel 1,3-disubstituted azetidine derivatives . Synth. Commun. 2008 , 38 , 1703 – 1717 .
   Web of Science ®Google Scholar
• Eastman Kodak company, Azonaline Masking couplers for photopghrphic materials. US, WO/1992/011575 Chem. Abstr. 1992 , 117 , 242650p .
   Google Scholar
• Fanning, Jr. , A. T. ; Roberts , T. D. A synthetic approach to benzenediazonium-2-thiocarboxylate . Tetrahedron Lett. 1971 , 12 , 805 – 808 .
   Google Scholar
• Kameswaran , V. Process and intermediates for the preparation of 1,3-oxzin-6-ones and uracils . WO/2000/049002 , Chem. Abstr. 2000 , 133 , 193159e .
   Google Scholar
• Amrein , K. ; Cai , J. ; Goodnow , R. A. Jr. ; Hunziker , D. ; Kuhn , B. ; Mayweg , A. ; Neidhart , W. Novel indazolone derivatives useful as 11β-HSD1 inhibitors . U.S. Patent 0069269 (2006) ; Chem. Abstr. 2007 , 144 , 312084r .
   Google Scholar