6'-(methylthio)-1'H-spiro-[indoline-3,3'-isoxazolo[3,4-d]-pyrimidine]-2,4'(5'H)-dione | 1414970-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6'-(methylthio)-1'H-spiro-[indoline-3,3'-isoxazolo[3,4-d]-pyrimidine]-2,4'(5'H)-dione
• 英文别名: 6-methylsulfanylspiro[1,5-dihydro-[1,2]oxazolo[3,4-d]pyrimidine-3,3'-1H-indole]-2',4-dione
• CAS: 1414970-30-1
• 化学式: C₁₃H₁₀N₄O₃S
• 分子量: 302.313
• InChiKey: SHTJMPFRYBDSCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6'-(methylthio)-1'H-spiro-[indoline-3,3'-isoxazolo[3,4-d]-pyrimidine]-2,4'(5'H)-dione 在 lithium aluminium deuteride 作用下， 生成 7a'-deutero-6'-(methylthio)-5',7a'-dihydro-1'H-spiro[indoline-3,3'-isoxazolo[3,4-d]pyrimidine]-2,4'(3a'H)-dione
  参考文献：
  名称：

  Identification and optimization of novel pyrimido-isoxazolidine and oxazine as selective hydride donors

  摘要：

  Two novel carbon skeletons (3S,3a'R)-6'-(methylthio)-5',7a'-dihydro-1'H-spiro[indoline-3,3'-isoxazolo [3,4-d]pyrimidine]-2,4'(3a'H)-dione (11a) and 3-(methylthio)-4a,5,7,11c-tetrahydropyrimido[4',5':3,4] [1,2]oxazino[6,5-b]indol-1(2H)-one (12a) are characterized as hydride donors. The generation of these hydride sources during the spiroannulation reaction between isatin (4) and pyrimidine (5) through the free radical mechanism, was confirmed by (i) the increase in the stoichiometric yields of 11 and 12 when the same reaction was carried out in the presence of free radical initiators (e.g., mCPBA) and (ii) the formation of oxazepine (14) when AIBN was used as free radical initiator. The PKIE [K-H/K-D] values 4.5 and 4.9 obtained when deuterated 11a (d) was used in the presence of TFA and TFA-d, respectively, suggest the hydride transfer step to be the rate determining step. These hydrides donors selectively reduce aldehyde in the presence of other reducible groups. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.105
• 作为产物：
  描述：

  基巯基-4-氨基-6-羟基嘧啶 、 靛红 在 间氯过氧苯甲酸 、 三氟乙酸 作用下， 反应 8.0h， 以40%的产率得到2,2'-bis(methylthio)-3H-spiro[pyrimido[4,5-b]quinoline-5,5'-pyrrolo[2,3-d]pyrimidine]-4,4',6'(3'H,7'H,10H)-trione
  参考文献：
  名称：

  Identification and optimization of novel pyrimido-isoxazolidine and oxazine as selective hydride donors

  摘要：

  Two novel carbon skeletons (3S,3a'R)-6'-(methylthio)-5',7a'-dihydro-1'H-spiro[indoline-3,3'-isoxazolo [3,4-d]pyrimidine]-2,4'(3a'H)-dione (11a) and 3-(methylthio)-4a,5,7,11c-tetrahydropyrimido[4',5':3,4] [1,2]oxazino[6,5-b]indol-1(2H)-one (12a) are characterized as hydride donors. The generation of these hydride sources during the spiroannulation reaction between isatin (4) and pyrimidine (5) through the free radical mechanism, was confirmed by (i) the increase in the stoichiometric yields of 11 and 12 when the same reaction was carried out in the presence of free radical initiators (e.g., mCPBA) and (ii) the formation of oxazepine (14) when AIBN was used as free radical initiator. The PKIE [K-H/K-D] values 4.5 and 4.9 obtained when deuterated 11a (d) was used in the presence of TFA and TFA-d, respectively, suggest the hydride transfer step to be the rate determining step. These hydrides donors selectively reduce aldehyde in the presence of other reducible groups. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.105

文献信息

• Identification and optimization of novel pyrimido-isoxazolidine and oxazine as selective hydride donors
  作者：Imran A. Khan、Vishal M. Balaramnavar、Anil K. Saxena

  DOI：10.1016/j.tet.2012.09.105

  日期：2012.12

  Two novel carbon skeletons (3S,3a'R)-6'-(methylthio)-5',7a'-dihydro-1'H-spiro[indoline-3,3'-isoxazolo [3,4-d]pyrimidine]-2,4'(3a'H)-dione (11a) and 3-(methylthio)-4a,5,7,11c-tetrahydropyrimido[4',5':3,4] [1,2]oxazino[6,5-b]indol-1(2H)-one (12a) are characterized as hydride donors. The generation of these hydride sources during the spiroannulation reaction between isatin (4) and pyrimidine (5) through the free radical mechanism, was confirmed by (i) the increase in the stoichiometric yields of 11 and 12 when the same reaction was carried out in the presence of free radical initiators (e.g., mCPBA) and (ii) the formation of oxazepine (14) when AIBN was used as free radical initiator. The PKIE [K-H/K-D] values 4.5 and 4.9 obtained when deuterated 11a (d) was used in the presence of TFA and TFA-d, respectively, suggest the hydride transfer step to be the rate determining step. These hydrides donors selectively reduce aldehyde in the presence of other reducible groups. (C) 2012 Elsevier Ltd. All rights reserved.