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Volumn 66, Issue 33, 2010, Pages 6383-6390

Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: A convenient synthon for the preparation of substituted 1,4-thiazepin-5-ones and piperidinones via the intermediacy of thioacids

Author keywords

Amide; Conjugate addition; Coupling; Radical reactions; Thioacid; Thioanhydride

Indexed keywords

1,4 THIAZEPIN 5 ONE; 2 [3 (TERT BUTYLOXYCARBONYLAMINO) 2 METHYLPROPYL]SUCCINIC THIOANHYDRIDE; ALKYL GROUP; DIHYDRO 3 (TRIPHENYLPHOSPHORANYLIDENE) 2,5 THIOPENDIONE; HALIDE; N (2 PHENYLETHYL) (4 METHYL 2 OXOPIPERIDIN 3 YL)ACETAMIDE; N (2 PHENYLETHYL) (5 OXO 7 METHYL 1,4 THIAZEPIN 6YL)ACETAMIDE; N (2 PHENYLETHYL) (5 OXO 7 PHENYL 1,4 THIAZEPIN 6YL)ACETAMIDE; N (2 PHENYLETHYL) (BENZO[B] 5 OXO 7 CYCLOPROPYL 1,4 THIAZEPIN 6YL)ACETAMIDE; N (2 PHENYLETHYL) (BENZO[B] 5 OXO 7 METHYL 1,4 THIAZEPIN 6YL)ACETAMIDE; N (2 PHENYLETHYL) (BENZO[B] 5 OXO 7 OCTANYL 1,4 THIAZEPIN 6YL)ACETAMIDE; N (2 PHENYLETHYL) (BENZO[B] 5 OXO 7 PHENYL 1,4 THIAZEPIN 6YL)ACETAMIDE; N [(4 METHYL 2 OXOPIPERIDIN 3 YL)ACETYL]PIPERIDINE; N [(5 OXO 7 METHYL 1,4 THIAZEPIN 6YL)ACETYL]PIPERIDINE; N [(5 OXO 7 PHENYL 1,4 THIAZEPIN 6YL)ACETYL]PIPERIDINE; N [(BENZO[B] 5 OXO 7 CYCLOPROPYL 1,4 THIAZEPIN 6YL)ACETYL]PIPERIDINE; N [(BENZO[B] 5 OXO 7 METHYL 1,4 THIAZEPIN 6YL)ACETYL]PIPERIDINE; N [(BENZO[B] 5 OXO 7 OCTANYL 1,4 THIAZEPIN 6YL)ACETYL]PIPERIDINE; N [(BENZO[B] 5 OXO 7 PHENYL 1,4 THIAZEPIN 6YL)ACETYL]PIPERIDINE; PIPERIDONE DERIVATIVE; THIAZEPINE DERIVATIVE; THIOACID; THIOL DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

EID: 77955656594     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.002     Document Type: Article
Times cited : (14)

References (75)
  • 4
    • 0003491442 scopus 로고
    • Methoden der Organischen Chemie
    • J. Falbe, Ed.; 4th ed. Thieme Stuttgart
    • W. Bauer, and K. Kühlein Methoden der Organischen Chemie J. Falbe, Ed.; Carbonsäure und Carbonsäure Derivate 4th ed. 1985 Thieme Stuttgart 832 890
    • (1985) Carbonsäure und Carbonsäure Derivate , pp. 832-890
    • Bauer, W.1    Kühlein, K.2
  • 54
    • 77955655139 scopus 로고    scopus 로고
    • note
    • Structures and stereochemistries were assigned based on a combination of one and two dimensional NMR experiments.
  • 67
    • 77955657291 scopus 로고    scopus 로고
    • note
    • This model assumes kinetic selectivity. We were unable to isolate the intermediate adducts before rearrangement to the thiazepinone system and so could not test for equilibration at that level. The cis- and trans- thiazepinones were somewhat resistant to equilibration under mild acid and basic conditions suggesting that at least equilibration did not occur after rearrangement.
  • 75
    • 77955663537 scopus 로고    scopus 로고
    • note
    • Equilibration of the isomers of 25 with sodium methoxide in hot methanol resulted in an equilibrium mixture favoring the trans-isomer indicating the kinetic nature of the products observed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.