- Tandem Michael-anti-Michael Addition-Mediated Orthogonal Strapping of Diynones: Regioselective Spirocyclopentannulation of Oxindoles and Pyrazolones and DFT Validation
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An efficient protocol involving the transformation of sequentially generated recursive anions from heterocyclic precursors to orthogonally strap diynones through one pot transition-metal-free spirocyclopentannulation has been devised, employing oxindoles
- Sarma, Manas Jyoti,Jindani, Sana,Ganguly, Bishwajit,Pabbaraja, Srihari,Mehta, Goverdhan
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p. 884 - 891
(2022/01/11)
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- Regiodivergent Hydration-Cyclization of Diynones under Gold Catalysis
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Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration-oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology in the total synthesis of polyporapyranone B was demonstrated.
- Mu?oz, Miguel A.,Sanz, Roberto,Solas, Marta,Suárez-Pantiga, Samuel
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supporting information
p. 7681 - 7687
(2020/10/12)
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- Ethyl lactate as a renewable carbonyl source for the synthesis of diynones
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Ethyl lactate, a sustainable feedstock, serves as a highly attractive building block for the synthesis of value-added chemicals such as skipped diynones and, after gold-catalyzed transposition, conjugated diynones. Green solvents are involved in all steps
- Solas, Marta,Suárez-Pantiga, Samuel,Sanz, Roberto
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supporting information
p. 213 - 218
(2019/01/28)
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- Transition Metal-Free Synthesis of 3-Alkynylpyrrole-2-carboxylates via Michael Addition/Intramolecular Cyclodehydration
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A transition metal-free and efficient method for the synthesis of 3-alkynylpyrrole-2-carboxylates from diynones and glycine esters or 2-aminoacetophenone hydrochloride has been developed. This transformation provides a large range of substituted pyrroles in good to excellent yields with the elimination of water as the only by-product. The detailed mechanistic studies elucidated that this transformation involves a Michael addition/intramolecular cyclodehydration process. (Figure presented.) .
- Teng, Qing-Hu,Xu, Yan-Li,Liang, Ying,Wang, Heng-Shan,Wang, Ying-Chun,Pan, Ying-Ming
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p. 1897 - 1902
(2016/07/06)
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- Bronsted acid catalyzed and NIS-promoted cyclization of diynones: Selective synthesis of 4-pyrone, 4-pyridone, and 3-pyrrolone derivatives
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Bronsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Bronsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions.
- Qiu, Yi-Feng,Yang, Fang,Qiu, Zi-Hang,Zhong, Mei-Jin,Wang, Li-Jing,Ye, Yu-Ying,Song, Bo,Liang, Yong-Min
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p. 12018 - 12028
(2014/01/06)
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- Synthesis of 1,4-diethynyl- and 1,1,4,4-tetraethynylbutatrienes
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In this paper, we report the synthesis and opto-electronic properties of differentially substituted 1,4-diethynyl- and 1,1,4,4-tetraethynylbuta-1,2,3- trienes. These novel chromophores greatly extend the series of building modules for oxidative coupling,
- Auffrant, Audrey,Diederich, Francois,Boudon, Corinne,Gisselbrecht, Jean-Paul,Gross, Maurice
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p. 3085 - 3105
(2007/10/03)
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