Convenient One-Pot Protocol for an Exclusive Synthesis of 4-Cyano/ethoxycarbonyl-2,2-dimethyl-2H-chromene and/or 3-Cyano/ethoxycarbonyl-2-isopropyl-benzo[b]furan from a Single Oxo-ylide

V.V.V.N.S.Rama Rao; R.Yadla; P.Shanthan Rao

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Convenient One-Pot Protocol for an Exclusive Synthesis of 4-Cyano/ethoxycarbonyl-2,2-dimethyl-2H-chromene and/or 3-Cyano/ethoxycarbonyl-2-isopropyl-benzo[b]furan from a Single Oxo-ylide

机译：方便的一锅操作方案，可从单一氧代内酯类化合物独家合成4-氰基/乙氧基羰基-2,2-二甲基-2H-色烯和/或3-氰基/乙氧基羰基-2-异丙基-苯并[b]呋喃

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[{2-(Fluoroaryloxy)-2-methyl-propanoyl}-(cyano/ethoxycarbonyl) methyl-ene]triphenylphosphoranes underwent microwave-assisted tandem intramolecular Wittig and Claisen rearrangement and internal cyclization reactions to afford fluoro-substituted 2,2-dimethyl-2H-chromenes and/or 2-isopropyl-benzo[b]furans in good yield.Upon controlled microwave irradiation in the presence of Nafion H catalyst in xylene,the oxo-ylides selectively formed 4-cyano/ethoxycarbonyl-2,2-dimethyl-2H-chromenes.Microwave irradiation of the same oxo-ylide in the presence of K2CO3 as catalyst or in a polar solvent-like sulfolane resulted in the exclusive formation of the corresponding ftuoro-substituted 3-cyano/ethoxycarbonyl-2-isopropyl-benzo[b]furans.

机译：[{2-（氟代芳氧基）-2-甲基丙酰基}-（氰基/乙氧基羰基）甲基-烯基]三苯基膦经微波辅助串联的分子内Wittig和Claisen重排和内部环化反应，得到氟取代的2,2-二甲基- 2H-色烯和/或2-异丙基-苯并[b]呋喃收率良好。在Nafion H催化剂存在下于二甲苯中进行微波控制下，氧代羰基选择性地形成4-氰基/乙氧基羰基-2,2-二甲基-2H-色烯。在K2CO3作为催化剂存在下或在极性溶剂样环丁砜中用微波辐照相同的羰基-叶立德导致相应的氟代取代的3-氰基/乙氧基羰基-2-异丙基-苯并[b]呋喃。

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《Synthetic Communications》 |2007年第6期|共9页
作者
V.V.V.N.S.Rama Rao; R.Yadla; P.Shanthan Rao;
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正文语种 eng
中图分类有机化学;
关键词
3-cyano-2-isopropyl-benzobfurans; 4-ethoxycarbonyl-2; 2-dimethyl-2H-chromene; intramolecular Wittig and Claisen rearrangement reactions; Nafion H;

机译：3-氰基-2-异丙基-苯并[b]呋喃;4-乙氧基羰基-2;2-二甲基-2H-色烯;分子内维蒂希和克莱森重排反应;Nafion H;

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1. Convenient One-Pot Protocol for an Exclusive Synthesis of 4-Cyano/ethoxycarbonyl-2,2-dimethyl-2H-chromene and/or 3-Cyano/ethoxycarbonyl-2-isopropyl-benzo[b]furan from a Single Oxo-ylide [J] . V.V.V.N.S.Rama Rao, R.Yadla, P.Shanthan Rao Synthetic Communications . 2007,第4a6期

机译：方便的一锅操作方案，可从单一氧代内酯类化合物独家合成4-氰基/乙氧基羰基-2,2-二甲基-2H-色烯和/或3-氰基/乙氧基羰基-2-异丙基-苯并[b]呋喃
2. A Convenient Synthesis of 2-Arylbenzo[b]furans from Aryl Halides and 2-Halophenols by Catalytic One-Pot Cascade Method [J] . Bosiak Mariusz Jan ACS catalysis . 2016,第4期

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Convenient One-Pot Protocol for an Exclusive Synthesis of 4-Cyano/ethoxycarbonyl-2,2-dimethyl-2H-chromene and/or 3-Cyano/ethoxycarbonyl-2-isopropyl-benzo[b]furan from a Single Oxo-ylide

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