2016
DOI: 10.1002/anie.201609726
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Development and Cycloaddition Reactivity of a New Class of Pyridine‐Based Mesoionic 1,3‐Dipole

Abstract: We describe here the development and structural characterization of a new type of mesoionic 1,3-dipole, which can be generated in the one-step reaction of imines with pyridine- or quinoline-based acid chlorides. Coupling the formation of these dipoles with alkyne cycloaddition can open a general and modular route to synthesize indolizines from combinations of available and diversifiable building blocks.

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Cited by 32 publications
(14 citation statements)
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References 69 publications
(12 reference statements)
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“…Traditional synthetic routes to indolizines mainly comprise the Scholtz or Chichibabin reactions. More recently, cycloaddition reactions (1,3‐dipolar cycloadditions), intramolecular cyclizations using acetic anhydride, formation of C3–C4 bond, formation of C1–C9 bond, and formation of C8–C9 bond have been reported . However, most of these methods suffer from some drawbacks, such as the formation of conjugate‐acid waste, narrow substrate scope, harsh reaction conditions, need for toxic transition‐metal catalysts and harmful organic solvents.…”
Section: Methodsmentioning
confidence: 99%
“…Traditional synthetic routes to indolizines mainly comprise the Scholtz or Chichibabin reactions. More recently, cycloaddition reactions (1,3‐dipolar cycloadditions), intramolecular cyclizations using acetic anhydride, formation of C3–C4 bond, formation of C1–C9 bond, and formation of C8–C9 bond have been reported . However, most of these methods suffer from some drawbacks, such as the formation of conjugate‐acid waste, narrow substrate scope, harsh reaction conditions, need for toxic transition‐metal catalysts and harmful organic solvents.…”
Section: Methodsmentioning
confidence: 99%
“…Thieme 等 [44] Avalos 等 [47][48][49] 报道了以 N,N,N Huseyin 等 [53] 以吡啶酰氯和(E)-N-乙基-1-(对甲苯 基)甲亚胺为原料, 在乙胺和三氯乙烷有机溶剂中 80 ℃ 反应约 12 h 后, 得到了 2-乙基-3-(对甲苯基)-2H-咪唑并 [1,5- [65] , 并将其作为潜在的杀螨剂 和杀虫剂进行研究. 专利中报道的大多数化合物在浓度 为 100 μg/mL 时对绿桃蚜的防效达 100% .…”
Section: 其它唑类介离子化合物unclassified
“…The 1,3-DC reactions between 1,3-dipoles and dipolarophiles are among the most important and extensively studied reactions in organic chemistry [40][41][42][43][44][45] recognized for their generality, scope, and mechanism, the judgment must be different" 47 .…”
Section: On the Reaction Mechanism Of 13-dipolar Cycloadditionsmentioning
confidence: 99%