• Archives of Pharmacal Research
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• 제20권6호
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• pp.647-651
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• 1997

The 6, 6-dibromopenam 6 was treated with $CH_{3}/MgBr$ and carbaldehyde 5 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 7, which was reacted with acetic anhybride to give acetoxy compound 8. The deacetobromination of 8 with zinc and acetic acid gave 6-exomethylenpenams, Z-isomer 9 and E-isomer 10, which were oxidized to sulfones 11 and 12 by m-CPBA. The p-methoxybenzyl compounds were deprotected by $AlCl_{3}$ and neutralized to give the sodium salts 13, 14, and 15.

• 대한화학회지
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• 제40권9호
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• pp.615-622
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• 1996

1-(Benzotriazol-1-yl)-1-benzenesulfonylmethane 1a에 LDA 및 methyl iodide를 작용시켜 1-(Benzotriazol-1-yl)-1-benzenesulfonylmethane 2a와 2-(Benzotriazol-1-yl)-2-benzenesulfonylpropane 2b를 각각 얻었다. 같은 방법으로 1-(Benzotriazol-1-yl)-1-benzenesulfonylmethane 1b로부터 1-(Benzotriazol-1-yl)-1-benzenesulfonylpropane 3a와 3-(Benzotriazol-1-yl)-3-benzenesulfonylpentane 3b를 얻었다. 한편, 1, 1-di(benzotriazol-1-yl)-1-arylmethane 4를 butyl lithiym과 diphenyl disulfide로 처리하여 1, 1-di(benzotriazol-1-yl)-1-aryl-1-thiophenoxymethane 5를 합성하였다. 1, 1-di(benzotriazol-1-yl)methane 8을 butyl lithiym과 diphenyl disulfide로 처리하여 1, 1-di(benzotriazol-1-yl)-1-thiophenoxymethane 9a와 1, 1-di(benzotriazol-1-yl)-1, 1-dithiophenoxymethane 9b를 각각 얻었다. 화합물 9a를 m-CPBA로 산화시켜 1, 1-di(benzotriazol-1-yl)-1-benzenesulfoxymethane 10a와 1, 1-di(benzotriazol-1-yl)-1-benzenesulfonylmethane 10b를 얻었다. 한편, 화합물 3b를 170.deg.C 에서 열분해시켜 3-toluenesulfonyl-2-pentene 11ㅇ르 얻었으며, 150.deg.C의 강철봄베속에서 3b를 과량의 물로 가수분해 시켰더니 sulfone의 C-N 및 C-S 결합 모두가 절단된 diethyl ketone 13a가 생성됨을 확인하였다.