- N-Heterocyclic carbene/photo-cocatalyzed oxidative Smiles rearrangement: Synthesis of aryl salicylates from: O -aryl salicylaldehydes
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The N-heterocyclic carbene/photo-cocatalyzed oxidative Smiles rearrangement of O-aryl salicylaldehydes was developed. Both electron-deficient and electron-rich aryls worked well as migrating groups, giving the corresponding aryl salicylates in good yields. This reaction features formation of two new C-O bonds and one C-O bond cleavage via metal-free oxidation of the Breslow intermediate using oxygen as the terminal oxidant and following the Smiles rearrangement under photocatalysis.
- Xia, Zi-Hao,Dai, Lei,Gao, Zhong-Hua,Ye, Song
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supporting information
p. 1525 - 1528
(2020/02/13)
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- Nonpeptide Angiotensin II Receptor Antagonist: N-imidazoles and Related Compounds as Potent Antihypertensives
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A series of compounds has been synthesized and demonstrated to be antagonists of the angiotensin II (AII) receptor.These compounds are structurally related to the N-(benzamidobenzyl)imidazoles and extend the scope of this new class of nonpeptide AII antag
- Carini, David J.,Duncia, John V.,Johnson, Alexander L.,Chiu, Andrew T.,Price, William A.,et al.
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p. 1330 - 1336
(2007/10/02)
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- Dibenzocyclooctene-, Dibenzochalcocine-, and Diarenochalconinediones
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2,2'-Oxybis-, -thiobis-, and -methylenebisbenzoic esters 2a-c react with methyllithium in ether to give low yields of 5H-dibenzochalcocine-5,7(6H)-diones 6a, 7a, and dibenzocyclooctene-5,7(6H,12H)-dione (8), respectively.Very good yields of such heterocycles with oxygen (6a-h, 37), sulfur (7a-h, 38) and selenium (36) as key atom are obtained when diaryl ethers (21, 22, 25), -sulfides (27, 29, 30), and -selenides (33) that contain 2'-acetyl- (or -propionyl-) and 2-methoxycarbonyl groups are treated with sodium hydride in boiling toluene.Analogously are prepared the dibenzoxonine-11,13(6H,12H)diones 62a-c and 7H-benzonaphthothionine-7,9-(8H)-dione (65) which are expanded by one ring member.In the analogous reaction of a corresponding benzophenone derivative 35, spiro-3(2H),3'-dione (41) is formed in a tandem reaction. - Under phase transfer conditions the dibenzochalcocinediones 6, 7, 36 and also the corresponding nitrogen cycles 5 react to give mixtures of C- (42-45) and O-alkyl derivatives (46-49).Methyllithium and diisobutylaluminium hydride provide the carbinols 50-54.With bromine and SO2Cl2, respectively, the methylene group is mono- or dihalogenated to the products 56, 57; defined nitration was only possible for the oxacycle 6a.
- Hellwinkel, Dieter,Bohnet, Siegbert
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p. 1151 - 1174
(2007/10/02)
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