REACTION OF 5,5-DIPHENYL-2-THIOHYDANTOIN WITH 1,4-DIBROMOBUTANE. THE CRYSTAL AND MOLECULAR STRUCTURE OF 2,3,4,5-TETRAHYDRO-7,7-DIPHENYLIMIDAZO-[2,1-b]-THIAZEPINE-8(7H)-ONE
REACTION OF 5,5-DIPHENYL-2-THIOHYDANTOIN WITH 1,4-DIBROMOBUTANE. THE CRYSTAL AND MOLECULAR STRUCTURE OF 2,3,4,5-TETRAHYDRO-7,7-DIPHENYLIMIDAZO-[2,1-b]-THIAZEPINE-8(7H)-ONE
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5,5-二苯基-2-乙内酰硫脲与 1,4-二溴丁烷的反应。
DOI：
10.1080/10426508908054895
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发表时间：
1989
影响因子：
1.3
通讯作者：
J. Karolak‐Wojciechowska
中科院分区：
文献类型：
--
作者：
K. Kieć‐Kononowicz;A. Zatorski;J. Karolak‐Wojciechowska
摘要 5,5-二苯基-2-硫代乙内酰脲 (1) (DPTH) 或其钾盐 (DPTH-K) 与 1,4-二溴丁烷反应生成两种异构双环产物：2,3,4,5-四氢-7,7-二苯基咪唑-[2,1-b]-硫氮杂卓-8(7H)-一 (6) 和 2,3,4,5-四氢-8,8-二苯基咪唑-[2,1-b]-硫氮杂卓-7(8)-一(7)，其比例取决于反应条件：[DPTH-K、EtOH、N-乙基哌啶；相转移催化条件：DPTH-K、Et3N、苯/水或DPTH丙酮/K2CO3]。化合物(6)在空间群P21/c中结晶，a = 10.4624(2)，b = 8.3643(1)，c = 18.4371(3) A β = 96.3(1)°。 (6)中的7元硫氮杂环采用无序链构象。讨论了DTPH(1)与二溴烷烃烷基化得到的异构化合物[(2),(3)],[(4),(5)]和[(6),(7)]的一些物理化学性质和一些影响其收率和比例的因素。
Abstract The reaction of 5,5-diphenyl-2-thiohydantoin (1) (DPTH) or its potassium salt (DPTH-K) with 1,4-dibromobutane gave two isomeric bicyclic products: 2,3,4,5-tetrahydro-7,7-diphenylimidazo-[2,1-b]-thiazepine-8(7H)-one (6) and 2,3,4,5-tetrahydro-8,8-diphenylimidazo-[2,1-b]-thiazepine-7(8)-one (7) in different ratios depending on the reaction conditions: [DPTH-K, EtOH, N-ethylpiperdine; phase transfer catalytical conditions: DPTH-K, Et3N, benzene/water or DPTH acetone/K2CO3]. Compound (6) crystallizes in the space group P21/c with a = 10.4624(2), b = 8.3643(1), c = 18.4371(3) A β = 96.3(1)°. The 7-membered thiazepine ring in (6) adopts a disordered chain conformation. The discussion of some physico-chemical properties and some factors showing the influence on the yield and ratios of isomeric compounds [(2), (3)], [(4), (5)] and [(6), (7)], obtained in the alkylation of DTPH (1) with dibromoalkanes, has been carried out.