Synthesis method of azetidine silicon precursor compound and method for synthesizing six-membered silicon-nitrogen heterocyclic compound by using azetidine silicon precursor compound
A heterocyclic compound and azetidine technology, which is applied in the synthesis of azetidine silicon precursor compounds and the synthesis of six-membered silicon nitrogen heterocyclic compounds, can solve the problems of poor applicability of functional groups, single synthesis technology, and reaction conditions Harshness and other problems, to achieve the effect of short reaction time, simple synthesis process, and avoid the generation of waste water
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Embodiment 1
[0068] This embodiment proposes a synthesis method of an azetidinine silicon precursor compound, comprising the following steps:
[0069] X1: under basic conditions, react the compound shown in general formula (I) with di-tert-butyl dicarbonate to obtain the compound shown in general formula (II) with Boc protecting group;
[0070] X2: Under alkaline conditions at 50-90°C, the resulting compound of formula (II) is subjected to a nucleophilic substitution reaction with a compound represented by general formula (III), and then the Boc protecting group is removed under acidic conditions, Obtain the compound represented by the general formula (IV), i.e. the azetidinine silicon precursor compound;
[0071] Among them, R 1 Representative groups are sulfonyl, acyl, alkyl or aryl;
[0072] R 2 Representative groups are linear alkyl, cyclic alkyl or aryl;
[0073] R 3 Representative groups are linear alkyl, cyclic alkyl or aryl;
[0074] X representative group is F, Cl, Br, I or ...
Embodiment 2
[0092] This embodiment provides a synthesis method of an azetidinine silicon precursor compound, comprising the following steps:
[0093] 1) The preparation of compound A, the reaction formula is as follows:
[0094]
[0095] 1.49g of sulfonamide and 92mg of 4-dimethylaminopyridine (catalyst) were added to 15mL of dichloromethane (solvent), then 0.97g of triethylamine (base) was added, and finally 1.78g of dicarbonic acid was slowly added dropwise After the addition of di-tert-butyl ester, react at room temperature for 2 hours; add 10 mL of water to back-quench the reaction, then extract twice with 20 mL of ethyl acetate, combine the organic phases, and use 20 mL of 1M hydrochloric acid and saturated saline Wash once respectively, anhydrous Na 2 SO 4 Drying, concentration under reduced pressure to remove the solvent, and recrystallization with ethyl acetate / petroleum ether system, to obtain 2.23 g of compound A as a white solid, with a yield of 94.5%;
[0096] 2) The pre...
Embodiment 3
[0103] Based on Example 2, this embodiment proposes a method for synthesizing a six-membered silicon azacyclic ring with an azetidine silicon precursor compound (compound C), including the following steps:
[0104] Wherein, the reaction formula is as follows:
[0105]
[0106] In the glove box, 58.4 mg of compound C, 7 mg of bistriphenylphosphine palladium dichloride (catalyst) and 12.6 mg of zinc iodide (stabilizer) were added to a 10 mL reaction tube, and then 0.5 mL of Xylene, 24.6 mg of phenylacetylene and 62 mg of 1,8-diazacyclo[5,4,0]undecene-7 (base, hydrogen abstraction to achieve intramolecular ring closure), sealed, at 120 ° C Reacted for 10 minutes, cooled to room temperature, concentrated under reduced pressure to remove the solvent, and then chromatographed on a 200-300 mesh silica gel column to obtain 52 mg of compound D (the final product of the six-membered silicon nitrogen heterocycle) as a white solid, with a yield of 72%.
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