Development of a Continuous Flow Synthesis of 2-Substituted Azetines and 3-Substituted Azetidines by Using a Common Synthetic Precursor

被引：21

作者：

Colella, Marco ^{[1
]}

Musci, Pantaleo ^{[1
]}

Cannillo, Debora ^{[1
]}

Spennacchio, Mauro ^{[1
]}

Aramini, Andrea ^{[2
]}

Degennaro, Leonardo ^{[1
]}

Luisi, Renzo ^{[1
]}

机构：

[1] Univ Bari A Moro, FLAME Lab, Flow Chem & Microreactor Technol Lab, Dept Pharm Drug Sci, I-70125 Bari, Italy

[2] Dompe Farmaceut SpA, Dept Discovery, I-67100 Laquila, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 20期

关键词：

ORTHO-DIRECTING ABILITY; FLASH CHEMISTRY; MICROREACTOR TECHNOLOGY; FUNCTIONALIZATION; SUBSTITUTION; HETEROCYCLES; ACCESS; RING; ARYL;

D O I：

10.1021/acs.joc.1c01297

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The generation and functionalization, under continuous flow conditions, of two different lithiated four-membered aza-heterocycles is reported. N-Boc-3-iodoazetidine acts as a common synthetic platform for the genesis of C3-lithiated azetidine and C2-lithiated azetine depending on the lithiation agent. Flow technology enables easy handling of such lithiated intermediates at much higher temperatures compared to batch processing. Flow technology combined with cyclopentylmethyl ether as an environmentally responsible solvent allows us to address sustainability concerns.

引用

页码：13943 / 13954

页数：12

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