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Volumn , Issue 17, 2006, Pages 2836-2840

A novel synthesis of the 2-aminoimidazol-4-carbaldehyde derivatives, versatile synthetic intermediates for 2-aminoimidazole alkaloids

Author keywords

2 aminoimidazol 4 carbaldehydes; Alkaloids; Cyclizations; Heterocycles; Total synthesis

Indexed keywords

1 TERT BUTOXYCARBONYL 2 TERT BUTOXYCARBONYLAMINOIMIDAZOL 4 CARBALDEHYDE; 2 AMINOIMIDAZOL 4 CARBALDEHYDE DERIVATIVE; 3 BROMO 1,1 DIMETHOXYPROPAN 2 ONE; ACETONE; ALDEHYDE DERIVATIVE; ALKALOID DERIVATIVE; DISPACAMIDE; GUANIDINE DERIVATIVE; HYMENIDIN; IMIDAZOLE DERIVATIVE; MONOBROMODISPACAMIDE; OROIDIN; TERT BUTOXYCARBONYLGUANIDINE; UNCLASSIFIED DRUG;

EID: 33750511308     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950250     Document Type: Article
Times cited : (23)

References (31)
  • 13
    • 33750503085 scopus 로고
    • Fr. Patent FR2681323, 1991
    • Alain, C. Fr. Patent FR2681323, 1991; Chem. Abstr. 1993, 119; 139229a.
    • (1993) Chem. Abstr. , vol.119
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  • 15
    • 33750522007 scopus 로고    scopus 로고
    • note
    • 5: C, 54.01; H, 6.80; N, 13.50. Found: C, 53.76; H, 6.63; N, 13.70.
  • 16
    • 33750504212 scopus 로고    scopus 로고
    • note
    • The reaction was continued until complete consumption of the starting material was ascertained by TLC analysis.
  • 18
    • 33750523609 scopus 로고    scopus 로고
    • note
    • The crystallographic data was deposited at the Cambridge Crystallographic Data Centre. The deposition number is CCDC 605791.
  • 19
    • 33750515639 scopus 로고    scopus 로고
    • note
    • When the reaction of 15 and 12a was examined in THF at 50 °C for 3 h (see below), 16 was obtained as an almost sole product in 68% yield along with a trace amount of 17.
  • 20
    • 33750494308 scopus 로고    scopus 로고
    • note
    • 2, EtOAc) afforded 14a as a colorless solid (159 mg, 62%). An analytical sample of 14a was prepared by recrystallization from EtOAc.
  • 21
    • 33750507906 scopus 로고    scopus 로고
    • note
    • We subjected 18a to tritylation, acetylation, triisopropylsilylation and methoxymethylation under the standard reaction conditions. Although formation of the desired compounds corresponding to 19a was observed in tritylation, acetylation and triisopropylsilylation, these products were found to be too unstable to be isolated in pure states. In the case of methoxymethylation, a complex mixture was obtained as the reaction product.
  • 24
    • 33750509617 scopus 로고    scopus 로고
    • note
    • 6 202-205 °C (dec.)].
  • 26
    • 33750513610 scopus 로고    scopus 로고
    • note
    • 19 amorphous solid).
  • 30
    • 33750519448 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of 3 and 4 synthesized by us clearly showed that both samples were contaminated by small amounts of the unnatural Z isomers (ca. 5%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.