Thermal behaviour of aryl γ-haloprcpargyl ethers
TL;DR: In this article, a systematic study of the behavior of aryl γ-halopropargyl ethers under thermal condition was undertaken, and the results showed that the transformation of these compounds yielded a mixture of products including 4-bromochromenes and chroman-4-ones.
About: This article is published in Tetrahedron.The article was published on 1989-01-01. It has received 18 citations till now. The article focuses on the topics: Ether & Aryl.
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TL;DR: Recently, Mao and co-workers were able to synthesize 6-bromo-8-ethoxy-3-nitro-2H-chromene 4 that exhibited potent antiproliferative activities against a panel of twelve tumor cell lines.
3 citations
TL;DR: In this article , a new alkyne functionalized pterin derivative was synthesized through a reaction of 7-chloropterin with propargyl alcohol in the presence of sodium hydride.
Abstract: A new alkyne functionalized pterin derivative was synthesized through a reaction of 7-chloropterin with propargyl alcohol in the presence of sodium hydride. The purity and chemical structure of the compound was validated by NMR (1H, 13C) spectroscopy, Mass (APCI source) spectrometry, elemental analysis, and X-ray crystallography. The title compound may be further functionalized by exploiting the yne moiety, for instance, using click chemistry. The novel pterin derivative, most notably, in contrast to typical pterin behavior, is now soluble or even well soluble in almost any solvent except water.
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61 citations
TL;DR: The Claisen rearrangement of aryl propargyl ethers in poly(ethylene glycol) -200 at 200°C affords products in good yields.
38 citations
TL;DR: In this paper, a one-pot synthesis of 4-chlorochromenes and chroman-4-ones was achieved from γ-chloropropargyl aryl ethers proceeding through Claisen rearrangement, depending upon the solvent of choice.
23 citations
TL;DR: Claisen Rearrangement of 2-Propinyl (3-Pyridyl) and Allyl (3pyridine) Ethers as mentioned in this paper showed that in both DMF and decane at 208° in a sealed tube, furopyridines and pyranopyridine were formed.
Abstract: Claisen Rearrangement of 2-Propinyl (3-Pyridyl) and Allyl (3-Pyridyl) Ethers1
2-Propinyl (3-pyridyl) ether (1), synthesized from the corresponding 3-pyridinol, was heated in DMF or decane at 208° in a sealed tube. In this way the furopyridines 2 and 3 were formed, and furthermore the pyranopyridine 4 if decane was used as solvent (Scheme 1). The same reactions took place with (2-methyl-3-pyridyl) 2-propinyl ether (14). In DMF only 15, and in decane 16 as well as 15 were formed (Scheme 3). The rearrangement of the pyridine derivative 17, which is substituted in both O-positions to the ether moiety, gave in both DMF and decane the diastereoisomeric tetracyclic compounds 18 and 19. The same kind of reaction took place with 25 (Scheme 4).
In the thermolysis of the allyl 3-pyridyl ether (27) cyclization was observed, too. The isolated product has the structure of the dihydrofuropyridine 28 (Scheme 6). The substituted allyl 3-pyridyl ether 30 reacted in the same way to the dihydrofuropyridine 31 (Scheme 6).
16 citations
TL;DR: In this paper, the authors present synthesis and properties of 4-Chloro and 4-Bromo-2H-chromenes and of 3-Halo 2Hchromenes.
Abstract: Durch Abspaltung von Bromwasserstoff entstehen aus den trans-3.4-Dihalogen-chromanen die entsprechenden 4-Halogen-2H-chromene 1–4. Die 3-Brom-2H-chromene 5 und 6 erhalt man durch Dehydratisierung der cis-3-Brom-4-hydroxy-chromane.
Synthesis and Properties of 4-Chloro- and 4-Bromo-2H-chromenes and of 3-Bromo-2H-chromenes
Dehydrobromination of trans-3,4-dihalochromans yields the 4-halo-2H-chromenes 1–4. Dehydration of cis-3-bromo-4-hydroxychromans leads to the 3-bromo-2H-chromenes 5 and 6.
15 citations