- Synthesis of 3-Unsubstituted Phthalides from Aryl Amides and Paraformaldehyde via Ruthenium(II)-Catalyzed C–H Activation
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A straightforward and convenient route has been developed for the synthesis of 3-unsubstituted phthalide derivatives from aryl amides and paraformaldehyde by ruthenium(II)-catalyzed C–H activation. The reaction proceeds through tandem ortho-hydroxymethylation of aryl amide and subsequent intramolecular lactonization.
- Zhou, Chao,Zhao, Junqi,Chen, Wenkun,Imerhasan, Mukhtar,Wang, Jun
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supporting information
p. 6485 - 6488
(2020/10/02)
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- A simple, rapid and efficient protocol for the synthesis of methylthiomethyl esters under Swern oxidation conditions
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A rapid, mild and high yielding method for the synthesis of methylthiomethyl esters is reported from the corresponding aliphatic, aromatic and unsaturated carboxylic acids under Swern oxidation conditions using dimethylsulfoxide, oxalyl chloride and triet
- Jadhav, Sunil B.,Ghosh, Usha
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p. 2485 - 2487
(2007/10/03)
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- Fast microwave promoted palladium-catalyzed synthesis of phthalides from bromobenzyl alcohols utilizing DMF and Mo(CO)6 as carbon monoxide sources
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A fast method utilizing in situ generated CO for the synthesis of phthalides has been developed. DMF and Mo(CO)6 were applied as two alternative CO-sources in these microwave promoted carbonylation-lactone formation reactions. Mo(CO)6 was found to be the more generally applicable CO-source and provided phthalides as well as dihydroisocoumarin, dihydroisoindone, and phthalimide from the corresponding aryl bromide via an efficient CO insertion within a 1h reaction time.
- Wu, Xiongyu,Mahalingam,Wan, Yiqian,Alterman, Mathias
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p. 4635 - 4638
(2007/10/03)
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- A New Synthesis of Phthalides by Internal Trapping in Ortho-Lithiated Carbamates Derived from Benzylic Alcohols
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The addition of t-BuLi to a low-temperature THF solution of o-bromocarbamates 2 leads to ortho-lithiated intermediates 3, in which internal trapping by the electrophile on the side chain then takes place.This novel Parham-type anionic cyclization procedure affords the variously substituted phthalides 5 in high yields and can also be used for the preparation of lactones 8, which are useful for the synthesis of aristocularine alkaloids.
- Paleo, M. Rita,Lamas, Carlos,Castedo, Luis,Dominguez, Domingo
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p. 2029 - 2033
(2007/10/02)
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- Electrochemical Oxidation of Aromatic Ethers. Part 9. Proof of the Mode of Aryl-Aryl Coupling in 4-Benzylisochroman-3-ones, and the Oxidative Reactions of 2-and 3-Aralkyl-1,2,3,4-tetrahydroisoquinolines
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The influence of the solvent upon the coupling reactions of 4-(3,4-dimethoxybenzyl)-6,7-dimethoxyisochroman-3-one has been studied and it is shown that formation of the product, 7a,8-dihydro-3,10,11-trimethoxy-2H-phenanthrofuran-2,7(5H)-dione, proceeds through a six-membered ring transition state.Anodic oxidation of 2-aralkyl-1,2,3,4-tetrahydroisoquinolines leads to cleavage of the aralkyl substituent, whereas 1,2,3,4-tetrahydro-6,7-dimethoxy-3-(3,4-dimethoxybenzyl)-2-methylisoquinoline cyclises to yield 1,2,3,4-tetrahydro-7,10,11-trimethoxy-3-methyl-2,8a-methanodibenzoazocin-6-one and its 1-hydroxy derivative.
- Majeed, Amera J.,Sainsbury, Malcolm,Hall, Stephen A.
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p. 833 - 837
(2007/10/02)
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