17402-80-1Relevant articles and documents
A new synthesis of pyrroles and porphyrins fused with aromatic rings
Ono, Noboru,Hironaga, Hideo,Ono, Kazuo,Kaneko, Syunichi,Murashima, Takashi,Ueda, Takahiro,Tsukamura, Chikanori,Ogawa, Takuji
, p. 417 - 423 (1996)
Pyrroles fused with aromatic rings (isoindole derivatives) have been readily prepared by the reaction of aromatic nitro compounds with ethyl isocyanoacetate in the presence of DBU. The ease of this reaction depends on the aromaticity of the starting nitro aromatics. Polycyclic aromatic nitro compounds such as 1-nitroacenaphthylene or 9-nitrophenanthrene are more reactive than simple nitro aromatics such as nitrobenzene or nitronaphthalenes and give the corresponding pyrroles in good yields. Pyrroles prepared by this method have been converted into porphyrins fused with various aromatic rings by the reduction with LiAlH4 followed by treatment with an acid catalyst and oxidation with chloranil or oxygen. Tetra-1,2-naphthoporphyrin has been prepared by the reaction of 2-nitro-3,4-dihydronaphthalene or 1-nitronaphthalene with ethyl isocyanoacetate followed by reduction, tetramerization and oxidation. Thus, highly conjugated porphyrins are readily prepared starting from aromatic nitro compounds, and their electronic and optical properties can be controlled by choice of the starting aromatic nitro compound.
Silver-Catalyzed Asymmetric Dearomatization of Electron-Deficient Heteroarenes via Interrupted Barton–Zard Reaction
Wan, Qian,Xie, Jia-Hao,You, Shu-Li,Yuan, Yao-Feng,Zheng, Chao
supporting information, p. 19730 - 19734 (2021/08/03)
Herein we report a catalytic asymmetric dearomatization reaction of electron-deficient heteroarenes with α-substituted isocyanoacetates through an interrupted Barton–Zard reaction. A range of optically active pyrrolo[3,4-b]indole derivatives was obtained
Palladium-Catalyzed Highly Stereoselective Dearomative [3 + 2] Cycloaddition of Nitrobenzofurans
Cheng, Qiang,Zhang, Hui-Jun,Yue, Wen-Jun,You, Shu-Li
supporting information, p. 428 - 436 (2017/09/22)
Stereoselective construction of highly functionalized heterocyclic molecules is an ongoing concern for the chemical community. Among the various strategies developed with this goal, catalytic asymmetric dearomatization, an attractive method for constucting cyclic molecules with multiple stereocenters from readily available aromatic compounds, has received extensive attention in recent years. Here, we report a highly stereoselective construction of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes via palladium-catalyzed dearomative [3 + 2] cycloaddition of nitrobenzofurans and nitrobenzothiophenes, respectively. Good to excellent yields (63%–92%), diastereoselectivity (13/1 → >20/1 dr), and enantioselectivity (75%–95% ee) were obtained, leading to products with vicinal stereogenic carbon centers. The reaction features wide substrate scope and diverse transformations of the products.
