A simple method for synthesizing 7-oxo-4-thia-1-azabicyclo (3.2. 0) heptane and its 6-methyl derivatives from ethyl cyanoacetate.

千葉卓男, 高橋工, /金子主税, C Kaneko

Index: Chiba; Takahashi; Sakaki; Kaneko Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 7 p. 3046 - 3049

Full Text: HTML

Citation Number: 1

Abstract

Ethyl cyanoacetate (1a) or its methyl derivatives (1b and 1c) were treated with HCl/EtOH to give the corresponding imidates (2a-2c). Treatment of the latter compounds with cysteamine gave ethyl 2-thiazoline-2-acetate (3a-3c), which by reduction with sodium cyanoborohydride

Related Articles:

Carbapenem biosynthesis: confirmation of stereochemical assignments and the role of CarC in the ring stereoinversion process from L-proline

[Nagamatsu, Tomohisa; Kunieda, Takehisa Chemical & Pharmaceutical Bulletin, 1988 , vol. 36, # 3 p. 1249 - 1251]

New condensing reagents

[Otsubo, Teruyuki; Matsukawa, Chiyoko; Ishizuka, Tadao; Kunieda, Takehisa Heterocycles, 1992 , vol. 33, # 1 p. 131 - 134]

A short synthesis of 7-oxo-4-thia-1-azabicyclo [3.2. 0] heptane. A basic skeleton of penicillin-type β-lactams

[Chiba, Takuo; Sakaki, Jun-ichi; Takahashi, Takumi; Kaneko, Chikara Chemistry Letters, 1985 , p. 659 - 660]

vic-Iodo Thiocyanates and Iodo Isothiocyanates. IX. A Synthesis of Penam and Other Polycyclic Β-Lactams

[Cambie, Richard C.; Clark, George R.; Jones, Tony C.; Rutledge, Peter S.; Strange, Gary A.; Woodgate, Paul D. Australian Journal of Chemistry, 1985 , vol. 38, # 5 p. 745 - 764]

vic-Iodo Thiocyanates and Iodo Isothiocyanates. IX. A Synthesis of Penam and Other Polycyclic Β-Lactams

[Cambie, Richard C.; Clark, George R.; Jones, Tony C.; Rutledge, Peter S.; Strange, Gary A.; Woodgate, Paul D. Australian Journal of Chemistry, 1985 , vol. 38, # 5 p. 745 - 764]

More Articles...