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Volumn , Issue 12, 2009, Pages 1997-2001

Synthesis of the first thiazolidine-condensed five-, six-, and seven-membered heterocycles via cyclization of vinylogous N-acyliminium ions

Author keywords

Cyclization; Fused ring systems; Iminium ions; Lactams; Neighboring group effects

Indexed keywords

ETHYL 2 (TETRAHYDROTHIAZOLO[4,3 B][1,3]THIAZIN 6 (2H) YLIDINE)ACETATE; ETHYL [7 METHYL 2H THIAZOLO[4,3 B]THIAZOL 5 (3H,7H,7AH) YLIDINE]ACETATE; FUSED RINGS WITH THREE OR MORE HETERO ATOMS; IMINE; NUCLEOPHILE; SULFUR; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 67651208211     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217532     Document Type: Article
Times cited : (18)

References (47)
  • 9
    • 2942574530 scopus 로고    scopus 로고
    • For recent reviews on iminium ion cyclization, see: a
    • For recent reviews on iminium ion cyclization, see: (a) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311.
    • (2004) Chem. Rev , vol.104 , pp. 2311
    • Royer, J.1    Bonin, M.2    Micouin, L.3
  • 24
    • 0040340791 scopus 로고
    • For this type of neighboring-group participation, see: a
    • For this type of neighboring-group participation, see: (a) Pasto, D. J.; Serve, M. P. J. Am. Chem. Soc. 1965, 87, 1515.
    • (1965) J. Am. Chem. Soc , vol.87 , pp. 1515
    • Pasto, D.J.1    Serve, M.P.2
  • 31
    • 67651237963 scopus 로고    scopus 로고
    • Typical Procedure for the Synthesis of (Z)-Ethyl 2-(Tetrahydrothiazolo[4,3-b][1,3]thiazin-6 (2H, ylidene)acetate (9f) The thioester 7f (50.5 mg, 0.17 mmol) was dissolved in dry EtOH (5 mL) and a solution of NaOEt (0.2 M in EtOH, 0.85 mL, 0.17 mmol) was added at r.t. with vigorous stirring. After hydrolysis to thiol, as evidenced by complete consumption of the reactant (ca. 15 min; TLC, the reaction mixture was cooled down to 0°C. Twofold mass excess of NaBH 4 (101 mg, 15-20 mmol equiv) was added, followed by 3 drops of 0.4 M HCl in EtOH. The addition of the same amount of acid was continued in regular 10 min intervals until the end of the reaction 45 min, when the reaction mixture was quenched with 1 M HCl in EtOH. The suspension was stirred for an additional 30 min at 0°C, diluted with H2O, extracted with CHCl 3, the organic phase separated, dried with Na2SO 4
    • + calcd: 246.06170; found: 246.06176 ± 0.24 ppm.
  • 32
    • 67651239989 scopus 로고    scopus 로고
    • Analytical Data of (Z)-Ethyl 2-{7-Methyl-2H-thiazolo[4,3- b]thiazol-5 (3H,7H,7aH)-ylidene}acetate (9c) Isolated in 37% yield as a mixture of trans- and cis-isomer in a 75:25 ratio. Compound trans-9c: 1H NMR (500 MHz, CDCl3, δ, 1.26 (3 H, t, J, 7.0 Hz, CH 3CH2, 1.49 (3 H, d, J, 6.5 Hz, CH 3CHS, 3.09-3.12 (1 H, m, CH2S, 3.15-3.20 (1 H, m, CH2S, 3.26-3.32 (1 H m, CH2N, 3.66 (1 H, dq, J1, 6.5 Hz, J2, 5.5 Hz, CHCH3S, 3.97 (1 H, ddd, J1, 9.0 Hz, J2, 6.0 Hz, J3, 3.0 Hz, CH2N) 4.16 (2 H, q, J, 7.0 Hz, CH2CH3, 4.89 (1 H, d, J, 5.5 Hz, CHSN, 5.07 (1 H, s, CH) ppm. 13C NMR 50.3 MHz, CDCl3
    • 3), 76.8 (CHSN), 84.8 (=CH), 163.8 (C=), 168.6 ppm.
  • 33
    • 34548150214 scopus 로고    scopus 로고
    • For recent examples of the 5-endo-trig mode ring-closing reaction, see: (a) Fuwa, H.; Sasaki, M. Org. Lett. 2007, 9, 3347.
    • For recent examples of the 5-endo-trig mode ring-closing reaction, see: (a) Fuwa, H.; Sasaki, M. Org. Lett. 2007, 9, 3347.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.