365261-27-4Relevant academic research and scientific papers
Method for synthesizing N-substitute-1, 2, 3, 6-tetrahydropyridine-5-boric acid ester
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Paragraph 0017, (2016/11/07)
The invention discloses a method for synthesizing N-substitute-1, 2, 3, 6-tetrahydropyridine-5-boric acid ester. According to the method, N-substitute-1, 2, 3, 6-tetrahydropyridine-5-carboxylic acid (ester) serves as the raw material, conducts addition with halogen and then is subjected to alkaline condition elimination to form alkenyl halide and then subjected to coupling with al boron ester under the condition of metal palladium catalyzation, and the N-substitute-1, 2, 3, 6-tetrahydropyridine-5-boric acid ester is obtained. According to the method, the obtained midbody alkenyl halide does not contain isomer, separation is easy to conduct, purity of an obtained product is high, and the method provides a simple way for synthesis of compounds of the type.
1-Methyl-1-azacyclohexa-2,3-diene(N-B)borane - Generation and interception of an unsymmetrical isodihydropyridine
Drinkuth, Stefan,Groetsch, Stefan,Peters, Eva-Maria,Peters, Karl,Christl, Manfred
, p. 2665 - 2670 (2007/10/03)
3-Bromo-1-methyl-1,2,5,6-tetrahydropyridine(N-B)borane (7) was prepared from 3-bromopyridine by conversion to 3-bromo-1-methylpyridinium iodide, hydrogenation of the latter with sodium tetrahydroborate and treatment of the resulting 3-bromo-1-methyl-1,2,5,6-tetrahydropyridine (6) with borane-dimethyl sulfide. Whereas no trapping product of the possible intermediate 1-methyl-1-azacyclohexa-2,3-diene (4) could be observed on treatment of 6 with potassium tert-butoxide in the presence of furan, the subjection of 7 to the same conditions produced the hexahydroepoxyquinoline derivatives 8a-c. Treatment of 7, dissolved in styrene, with sodium bis(trimethylsilyl)amide furnished the hexahydrocyclobutapyridine derivatives 9a-c. The six-membered cycloallene 1-methyl-1-azacyclohexa-2,3-diene(N-B)borane (10) must be regarded as the key intermediate en route to 8 and 9.
