A kind of c-3 iodo-indolizine compounds and preparation method thereof
A compound and indolizine technology, which is applied in the field of C-3-position iodine indolizine compounds and their preparation, can solve the problems of complex reaction and insufficient substrate applicability, and achieve the effects of easy availability of raw materials and simple method.
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[0028] The present invention provides a kind of preparation method of C-3 iodo-indolizine compound, comprising the following steps:
[0029] After mixing iodine, 2-pyridine acetate, acrylate and base in an organic solvent, the heating reaction is carried out to obtain the C-3 iodoindolizine compound.
[0030] In the present invention, the structure of the C-3 iodo-indolizine compound is shown in formula I:
[0031]
[0032] R in Formula I 1 is methyl, ethyl, isopropyl or n-butyl;
[0033] R 2 is methyl, ethyl, n-butyl, phenyl or benzyl.
[0034] In the present invention, the structure of the iodoindolizine compound at the C-3 position is preferably any one of formulas I-1 to I-8:
[0035]
[0036] In the present invention, the structure of the 2-pyridine acetate is shown in formula II:
[0037] where R 1 is methyl, ethyl, isopropyl or n-butyl.
[0038] In the present invention, the 2-pyridine acetate preferably includes methyl 2-pyridine acetate, ethyl 2-pyridin...
Embodiment 1～8
[0061] Add iodine, alkali, 2-pyridine acetate, acrylate and 2mL organic solvent into a 10mL sealed tube according to the raw material ratio in Table 1, mix and stir evenly, and then heat. The heating temperature and heating time are shown in Table 2 shown. After the reaction was completed, adding a mass concentration of 10% sodium thiosulfate aqueous solution to the obtained reaction feed liquid was used for extraction with ethyl acetate, and the organic phase obtained by the extraction was dried with anhydrous sodium sulfate and then the supernatant was taken. After column chromatography treatment (the eluent for column chromatography treatment is a mixed solution of petroleum ether and ethyl acetate, the volume ratio of petroleum ether and ethyl acetate is 1:10), the purified C-3 iodo neutral nitrogen Indenic compounds, the structures of the products obtained in Examples 1 to 8 are shown in I-1 to I-8 respectively.
[0062] The raw material proportioning of table 1 embodime...
Embodiment 1
[0071] The structure and nuclear magnetic resonance (NMR) of the prepared C-3 iodo-indolizine compounds 1 H NMR and 13 C NMR) detection data are:
[0072]
[0073] 1 H NMR (600MHz, CDCl 3 )δ8.12(d, J=4.8Hz, 1H), 8.11(d, J=3.3Hz, 1H), 7.14(t, J=8.3Hz, 1H), 6.89(t, J=7.5Hz, 1H) ,3.98(s,3H),3.88(s,3H).
[0074] 13 C NMR (150MHz, CDCl 3 )δ166.0, 163.3, 138.2, 137.3, 129.6, 127.2, 124.0, 120.2, 114.5, 104.6, 52.8, 51.5.
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