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Volumn , Issue 1, 2008, Pages 0108-0110

A facile synthesis of 1-arenesulfonylazetidines through reaction of 1-arenesulfonylaziridines with dimethylsulfoxonium methylide generated under microwave irradiation

Author keywords

Azo compounds; Heterocycles; Ring expansion; Sulfur; Ylides

Indexed keywords

1 ARENESULFONYLAZETIDINE; 1 ARENESULFONYLAZIRIDINE; 2 (4 BROMOPHENYL) 1 (4 TULOENESULFONYL)AZETIDINE; 2 (4 CHLOROPHENYL) 1 (4 TULOENESULFONYL)AZETIDINE; 2 (4 METHYLPHENYL) 1 (4 TULOENESULFONYL)AZETIDINE; 2 HEXYL 1 (4 TULOENESULFONYL)AZETIDINE; 2 METHYL 3 PHENYL 1 (4 TOLUENESULFONYL)AZETIDINE; ALUMINUM OXIDE; AZETIDINE DERIVATIVE; DIMETHYLSULFOXONIUM METHYLIDE; ORGANIC COMPOUND; UNCLASSIFIED DRUG;

EID: 38549086843     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1000838     Document Type: Article
Times cited : (34)

References (40)
  • 8
    • 38549128538 scopus 로고    scopus 로고
    • Patent, WO2006107941
    • Brunette, S. R. Ger. Patent, WO2006107941, 2006.
    • (2006)
    • Brunette, S.R.G.1
  • 14
    • 84993879918 scopus 로고
    • For four-membered heterocyclic ring system, see
    • For four-membered heterocyclic ring system, see: Parrick, J. Prog. Heterocycl. Chem. 1991, 3, 58.
    • (1991) Prog. Heterocycl. Chem , vol.3 , pp. 58
    • Parrick, J.1
  • 32
    • 38549134735 scopus 로고    scopus 로고
    • PhD Thesis; Indian Institute of Technology Delhi: India
    • Singh, A. PhD Thesis; Indian Institute of Technology Delhi: India, 2005.
    • (2005)
    • Singh, A.1
  • 33
    • 38549128600 scopus 로고    scopus 로고
    • General Method for the Synthesis of 1-Arenesulfonylazetidines: The pertinent aziridine (1 mmol, trimethylsulfoxonium iodide (3 mmol) and KOH (3 mmol) were loaded on neutral alumina (0.5 mmol) solid support. This mixture was irradiated with microwaves for the specified time (Table 1, Only a single product (as shown by TLC) was formed. The reaction was quenched by addition of cold H2O. The product was extracted with EtOAc and purified by simple crystallization or through column chromatography on silica gel. cis-2-Methyl-3-phenyl-1-(4-toluenesulfonyl)azetidine (3f, white crystalline solid; mp 105-106°C; yield: 79, IR: 1333, 1164 (SO 2) cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.65 (m, 5 H, 7.32 (s, 4 H, 4.26 (q, J, 7 Hz, 1 H, 3.93 (distorted d, J, 6 Hz, 2 H, 3.41 (m, 1 H, 2.39 (s, 3 H, 0.98 (d, J, 7 Hz, 3 H, 13C NMR 75 MHz, CDCl3, δ, 127.2-137
    • +].
  • 34
    • 38549169806 scopus 로고    scopus 로고
    • The reaction vials were placed in the MW reactor supplied with a safety valve for release of overpressure
    • The reaction vials were placed in the MW reactor supplied with a safety valve for release of overpressure.
  • 35
    • 38549161448 scopus 로고    scopus 로고
    • After the set temperature of 90°C is reached, the power regulates itself to maintain the reaction temperature.
    • After the set temperature of 90°C is reached, the power regulates itself to maintain the reaction temperature.
  • 36
    • 38549156390 scopus 로고    scopus 로고
    • I.C.I. Ltd., FR 1544970, 1968, Chem. Abstr. 1970, 72, 12545.
    • I.C.I. Ltd., FR 1544970, 1968, Chem. Abstr. 1970, 72, 12545.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.