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Volumn , Issue 19, 2007, Pages 2961-2964

Synthesis of benzo[b][1,4]thiazines by hetero-Diels-Alder reaction of o-iminothioquinones

Author keywords

Diels Alder; Electrophilic aromatic substitutions; Heterocycles; o iminothioquinones; Phthalimidesulfenyl chloride

Indexed keywords

2 IMINOTHIOQUINONE DERIVATIVE; BENZO[B] [1,4]THIAZINE DERIVATIVE; QUINONE DERIVATIVE; THIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 37249059786     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992360     Document Type: Article
Times cited : (5)

References (21)
  • 16
    • 0141542721 scopus 로고    scopus 로고
    • To the best of our knowledge only an example of a dienic o-iminothioquinone has been reported in the literature: Diep, V.; Dannenberg, J. J.; Franck, R. W. J. Org. Chem. 2003, 68, 7907.
    • To the best of our knowledge only an example of a dienic o-iminothioquinone has been reported in the literature: Diep, V.; Dannenberg, J. J.; Franck, R. W. J. Org. Chem. 2003, 68, 7907.
  • 19
    • 37249080430 scopus 로고    scopus 로고
    • A small amount of the bis-sulfenylated derivative 5-10, was also isolated
    • A small amount of the bis-sulfenylated derivative (5-10%) was also isolated.
  • 20
    • 37249013573 scopus 로고    scopus 로고
    • The following procedures for the preparation of 3a, by sulfenylation of 2a with sulfenyl chloride 1, and synthesis of thiazine 5e, by cycloaddition of an o-iminothioquinone with p-methoxystyrene (4e, can be regarded as general procedures as well. Synthesis of N-Thiophthalimide 3a: A solution of PhthNSCl (1; 0.788 g, 3.47 mmol) in anhyd CHCl3 (10 mL) was added to a solution of N-tosyl aniline 2a (0.890 g, 2.89 mmol) in anhyd CHCl3 (10 mL, The reaction mixture was stirred at r.t. for 3.5 h, diluted with CH2Cl2, washed with a sat. solution of NaHCO3, and H2O, and dried over Na2SO 4. The material obtained after evaporation of the solvent was purified by flash chromatography on silica gel using CHCl3 as eluent. o-N-Tosyl-N-thiophthalimide 3a was obtained as a white powder 0.390
    • 2: C, 61.70; H, 5.80; N, 2.88. Found: C, 61.96; H, 5.75; N, 2.96.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.