Flow-Assisted Synthesis of Bicyclic Aziridines via Photochemical Transformation of Pyridinium Salts,Organic Process Research & Development

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Flow-Assisted Synthesis of Bicyclic Aziridines via Photochemical Transformation of Pyridinium Salts
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2018-03-06 00:00:00 , DOI: 10.1021/acs.oprd.8b00036
Filipa Siopa ₁ , João P. M. António ₁ , Carlos A. M. Afonso ₁

Affiliation

Herein is described the development and comparison of homemade continuous-flow reactors, a fluorinated ethylene propylene tube (FEP) reactor (internal diameter of 0.4 cm) and two parallel quartz reactors containing two different internal diameters (0.4 and 0.2 cm), and their application to the photochemical transformation of 1-n-butyl- and 1-allylpyridinium bromide salts (1a and 1b, respectively) to the corresponding α-hydroxycyclopentenoaziridines (6-azabicyclo[3.1.0]hex-3-en-2-ols) 2a and 2b. Under recirculating conditions, the FEP reactor allowed the production of a greater quantity of bicyclic aziridine (3.2 g), while the quartz reactor with the same diameter furnished the best productivity results (3.7 g L^–1 h^–1). In addition, the FEP reactor operated efficiently under circulating conditions (1.75 L of 1a) for 4.5 days (residence time of 17.9 h), allowing the production of 2a at a rate of 2 g/day (62–93% conversion).

中文翻译：

流辅助双环彭孝军，合成通过吡啶盐的光化学变化

本文描述了自制连续流反应器，氟化乙烯丙烯管（FEP）反应器（内径为0.4厘米）和两个包含两个不同内径（0.4和0.2厘米）的平行石英反应器的开发和比较及其应用到1-正丁基和1-烯丙基溴化溴化物盐（分别为1a和1b）的光化学转化为相应的α-羟基环戊烯氮丙啶（6-氮杂双环[3.1.0] hex-3-en-2-ols）2a和2b。在再循环条件下，FEP反应器可生产更多量的双环氮丙啶（3.2 g），而相同直径的石英反应器可提供最佳的生产率结果（3.7 g L ^–1 h ^–1）。此外，FEP反应器在循环条件下（1.75 L，1a）可有效运行4.5天（停留时间为17.9 h），从而以2 g /天的速度生产2a（转化率为62-93％）。

更新日期：2018-03-06

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