Direct Functionalization of Azepane via Azomethine Ylides: A Highly Efficient Synthesis of Spirooxindoles Bearing a 1‐Azabicyclo[5.3.0]decane Moiety

Meng, Xiangtai; Du, Yuguo; Zhang, Qi; Yu, Aimin; Zhang, Youquan; Jia, Jiru; Liu, Xiujie

doi:10.1002/ajoc.201700384

Asian J Org Chem

2017

DOI: 10.1002/ajoc.201700384

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Direct Functionalization of Azepane via Azomethine Ylides: A Highly Efficient Synthesis of Spirooxindoles Bearing a 1‐Azabicyclo[5.3.0]decane Moiety

Xiangtai Meng

Yuguo Du

Qi Zhang

et al.

Abstract: Spirooxindoles bearing a1 -azabicyclo[5.3.0]decane moiety were synthesized in one step via direct functionalizationo ft he azepane withoutatransition metal or oxidants. This is an efficient process for the synthesiso f fused 7/5-heterobicyclic systemsi no ne step. Furthermore, cycloaddition of the in-situ-generated azomethine ylide only proceededfor alkenyls ulfone dipolarophiles.

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Cited by 5 publications

References 88 publications

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Solvent-Controlled Switchable Domino Reactions of MBH Carbonate: Synthesis of Benzothiophene Fused α-Pyran, 2,3-Dihydrooxepine, and Oxatricyclodecene Derivatives

Jia

et al. 2017

Org. Lett.

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Solvent-controlled switchable domino reactions between 2-alkylidenebenzothiophene-3(2H)-ones and Morita-Baylis-Hillamn (MBH) carbonate were developed. All domino reactions exhibited excellent regioselectivity, producing a broad spectrum of benzothiophene-fused α-pyran, 2,3-dihydrooxepine, and oxatricyclodecene derivatives. Furthermore, [4 + 2], [4 + 3], and related domino reactions from identical substrates can be controlled.

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Solvent-Controlled Switchable Domino Reactions of MBH Carbonate: Synthesis of Benzothiophene Fused α-Pyran, 2,3-Dihydrooxepine, and Oxatricyclodecene Derivatives

Jia

et al. 2017

Org. Lett.

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Phosphine-catalyzed [4 + 2] annulation of γ-benzyl allenoates: facile synthesis of benzothieno[3,2-b]pyran derivatives

Meng

2018

Org. Biomol. Chem.

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An efficient tris(4-methoxyphenyl)phosphine-catalyzed domino reaction between γ-benzyl allenoates and ethyl (Z)-2-(3-oxobenzo[b]thiophen-2(3H)-ylidene)acetate has been developed, which produces a series of 2H-benzo[4,5]thieno[3,2-b]pyran derivatives in high yields. The substrate scope includes both electron-withdrawing (e.g., halogen) and electron-donating (e.g., methoxy) groups on both the benzothiophene and allenoate moieties. The reaction can also be performed on the gram scale with good yield (e.g., 77%). In this reaction, γ-substituted allenoate acts as a two-carbon synthon, in a manner rarely reported in the literature to date.

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Darzens reaction of thioisatins and sulfonium salts: approach to the synthesis of thiochromenone derivatives with anticancer potency

et al. 2018

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A new Darzens reaction of thioisatins and sulfonium salts has, for the first time, been reported. This reaction allows efficient access to thiochromenone derivatives in good to excellent yields under mild reaction conditions. The substrate scope includes both electron-withdrawing and electron-donating groups on both the thioisatins and sulfonium salts. Moreover, some of the synthesized thiochromenone derivatives have been found to show potent anticancer activities against six different cancer cell lines using the methylthiazoltetrazolium (MTT) assay.

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Direct Functionalization of Azepane via Azomethine Ylides: A Highly Efficient Synthesis of Spirooxindoles Bearing a 1‐Azabicyclo[5.3.0]decane Moiety

Cited by 5 publications

References 88 publications

Solvent-Controlled Switchable Domino Reactions of MBH Carbonate: Synthesis of Benzothiophene Fused α-Pyran, 2,3-Dihydrooxepine, and Oxatricyclodecene Derivatives

Solvent-Controlled Switchable Domino Reactions of MBH Carbonate: Synthesis of Benzothiophene Fused α-Pyran, 2,3-Dihydrooxepine, and Oxatricyclodecene Derivatives

Phosphine-catalyzed [4 + 2] annulation of γ-benzyl allenoates: facile synthesis of benzothieno[3,2-b]pyran derivatives

Darzens reaction of thioisatins and sulfonium salts: approach to the synthesis of thiochromenone derivatives with anticancer potency

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