- Regiospecific synthesis of polysubstituted furans with mono- to tricarboxylates from various sulfonium acylmethylides and acetylenic esters
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Polysubstituted furans were prepared in moderate to good yields from various sulfur ylides and alkyl acetylenic carboxylates. The direct reactions of dimethylsulfonium acylmethylides with dialkyl acetylenedicarboxylates afforded dialkyl furan-3,4-dicarboxylates through a tandem sequence of Michael addition, intramolecular nucleophilic addition, 4π ring opening, intramolecular Michael addition, and elimination. The method was extended to synthesize furan-3-carboxylate, -2,4-dicarboxylates, and -2,3,4-tricarboxylates as well. The current method provides a direct and simple strategy in the synthesis of structurally diverse polysubstituted furans with mono to tricarboxylate groups from safe and readily available dimethylsulfonium acylmethylides and different alkyl acetylenic carboxylates.
- Dong, Jun,Du, Hongguang,Xu, Jiaxi
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p. 25034 - 25038
(2019/08/22)
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- A mild, convenient and efficient single-step method for the synthesis of polysubstituted furans via ammonium ylide routes
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A new and convenient cyclization method for the synthesis of polysubstituted furans in a single-step via ammonium ylide routes was reported. In this process, dimethyl acetylenedicarboxylate reacted with ammonium ylide to produce polysubstituted furan in the presence of anhydrous K2CO 3 at room temperature. It is very economical, environmentally friendly and very easy to carry out. Georg Thieme Verlag Stuttgart.
- Fan, Mingjin,Guo, Lina,Liu, Xueyuan,Liu, Weimin,Liang, Yongmin
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p. 391 - 396
(2007/10/03)
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- Synthesis and cycloadditions of 9H-furo[3,4-b][1]benzo(thio)pyran-9-ones: Furan ring formation by a novel hydrolytically induced cycloreversion
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C-2 lithiation of acetals 2 followed by trapping with aldehydes gives 3. Subsequent unmasking of the acetal function provides furobenzo(thio)pyrans 4, cycloadditions of which have been investigated.
- Daia, G.Elena,Gabbutt, Christopher D.,Hepworth, John D.,Heron, B.Mark,Hibbs, David E.,Hursthouse, Michael B.
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p. 4507 - 4510
(2007/10/03)
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- SYNTHESIS AND ELECTROPHILIC SUBSTITUTION REACTIONS OF 2-ARYL-3,4-BIS(CARBOMETHOXY)FURANS
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The thermal decomposition of the products of hydrogenation of the adducts obtained from arylfurans and dimethyl acetylenedicarboxylate leads to the formation of 2-aryl-3,4-bis(carbomethoxy)furans.The bromination of these compounds takes place in the 5 pos
- Oleinik, A. F.,Adamskaya, E. V.,Novitskii, K. Yu.
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p. 337 - 340
(2007/10/02)
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