Syntheses and reactivity of trans-6-azabicyclo[3.1.0]hexan-2-ol derivatives and indanol[1,2-b]aziridine. Structural analogs of mitomycin C
Syntheses and reactivity of trans-6-azabicyclo[3.1.0]hexan-2-ol derivatives and indanol[1,2-b]aziridine. Structural analogs of mitomycin C
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反式6-氮杂双环[3.1.0]己-2-醇衍生物和茚满醇[1,2-b]氮丙啶的合成和反应性。
DOI：
10.1021/jo00165a015
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发表时间：
1983
影响因子：
3.6
通讯作者：
H. Kohn
中科院分区：
文献类型：
--
作者：
I. Chiu;H. Kohn
本文报道了三个稠合的氮杂环丙烷（4-6）的合成和反应性。反式-6-氮杂双环[3.1. 0]己-2-醇（4）和顺-2-甲基-铁-6-氮杂双环[3.1. 0]己-2-醇（5）在HCl和HCl O 4酸水溶液中进行氮丙啶环的区域和立体特异性开环。在每种情况下，反应在碳-5处进行，得到反式开环产物。相应地，用HCl 04酸水溶液处理茚并[1，2-B]氮丙啶（6）得到顺式和反式-2-氨基-1-茚满醇的2.7：1混合物（分别为39和40）。将这些结果与先前证明的丝裂霉素C酸促水解的结果进行比较（1），表明后者的水解可能是先失去甲醇得到吲哚醌，然后通过SN 1型过程使氮丙啶环区域特异性开环。
The synthesis and reactivity of three annelated aziridines (4-6) are described. irans-6-Azabicyclo [3.1. 0] hexan-2-ol (4) and cis-2-methyl-irons-6-azabicyclo [3.1. 0] hexan-2-ol (5) undergo regio-and stereospecific ring opening of the aziridine ring in aqueous HC1 and HC104 acid solutions. In each case, reaction proceeds at carbon-5 to give the trans-ring-opened product. Correspondingly, treatment of indano [l, 2-b] aziridine (6) with aqueous HC104 acid gave a 2.7: 1 mixture of cis-and írons-2-amino-l-indanol (39 and 40, respectively). Comparison of these results with those previously reportedfor the acid-promoted hydrolysis of mitomycin C (1) suggests that hydrolysis in the latter case may proceed by initial loss of methanol to give the indoloquinone, followed by regiospecific ring opening of the aziridine ring by an SNl-type process.