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Synthesis and Crystal Structure of Ethyl (2-Amino-4-(2-chlorophenyl)-4H-benzo-[h]-chromene-2-yl) Formate

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Chinese Journal of Structural Chemistry 2004年第3期23卷 278-281页

作者： Wang XIangshan Shi Daqing tu shujiang Yao Changsheng Department of Chemistry Xuzhou Normal UniversityXuzhou 221116China Key Laboratory of Biotechnology on Medical Plant XuzhouJiangsu 221116China

The title compound ethyl (2-amino-4-(2-chlorophenyl)-4H-benzo-[h]-chromene-2-yl) formate (C22H18ClNO3, Mr = 379.82) was synthesized and characterized by X-ray single-crystal diffraction analysis. The crystal belongs to monoclinic, space group C2/c with a = 25.168(4), b = 9.584(1), c = 16.503(3) ? b = 111.14(1), Z = 8, V = 3713(1) 3, Dc = 1.359 g/cm3, m(MoKa) = 0.228 mm-1, F(000) = 1584, R = 0.0565 and wR = 0.1320 for 1749 observed reflections (I > 2s(I)). X-ray analysis reveals that the C(1), C(2), C(3), C(4), C(5) and O(1) atoms form a six-membered ring which adopts a boat conformation. In this ring, the bond distances of C(1)C(2) and C(4)C(5) are 1.356(4) and 1.357(4) ? respectively, indicating they are C=C double bonds. In addition, there exist intra- and intermolecular hydrogen bonds in the crystal structure.

关键词： crystal structure, 4H-benzo-[h]-chromene, synthesis

A Highly Diastereoselective Three-component Domino Reac- tion in Water Yielding Poly-substituted 4,5-Dihydropyrroles

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Chinese Journal of Chemistry 2013年第8期31卷 1039-1044页

作者： Guangjing Tong Haiwei Xu Wei Fan Bo Jiang Shuliang Wang shujiang tu School of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials Jiangsu Normal University Xuzhou Jiangsu 211116 China Jiangsu Provincial Xuzhou Pharmaceutical Vocational College Xuzhou Jiangsu 221116 China

An efficient methodology for highly diastereoselective synthesis ofpoly-substituted 4,5-dihydropyrrole deriva- tives from readily available common reactants in water has been developed. During domino processes, the forma- tion of pyrrole skeleton and its C2-hydroxylation and C3-arylamination were readily achieved via metal-free [3 ＋2] heterocyclization in a one-pot operation.

关键词： highly diastereoselective 4,5-dihydropyrroles hydroxylation arylamination domino reactions

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Radical-Enabled Bicyclization Cascades of Oxygen-Tethered 1,7-Enynes Leading to Skeletally Diverse Polycyclic Chromen-2-ones

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Chinese Journal of Chemistry 2017年第3期35卷 323-334页

作者： Bo Jiang Jie Li Yuanyuan Pan Wenjuan Hao Guigen Li shujiang tu School of Chemistry and Chemical Engineering Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials Jiangsu Normal University Xuzhou Jiangsu 221116 China Department of Chemistry and Biochemistry Texas Tech University Lubbock Texas 79409-1061 United States Institute of Chemistry & BioMedical Sciences Collaborative Innovation Center of Chemistry for Life Sciences Nanjing University Nanjing Jiangsu 210093 China

Catalytic bicyclization cascades of oxygen-tethered 1,7-enynes with simple cycloalkanes or aryl sulfonhydrazides have been established via subsequent multiple C-C bond-forming events from alkynyl/alkenyl functions, delivering a series of densely functionalized tetracyclic chromen-2-ones in a functional-group-compatible manner. In the former, Fe-catalyzed spiro-bicyclization involves radical addition, 6-exo-dig cyclization, H-abstraction and 5-endo-trig cyclization sequences under mild conditions, resulting in new spiro-fused cyclopenta[c]chromen-2-ones via dual α,α-C(sp3)-H abstractions. The latter enables in-situ sulfonylation and desulfonylation of oxygen-tethered 1,7-enynes to realize the construction of multiple C-C bonds, thereby leading to the formation of naphtho[2,3-c]chromen-6-ones.

关键词： bicyclization radical reaction 1 7-enynes fused chromen-2-ones C(sp3)-H functionalization

Multicomponent Domino [4＋1＋1] Carbocyclization Providing an Efficient and Regioselective Strategy to Fluoren-9-ones

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Chinese Journal of Chemistry 2013年第6期31卷 737-744页

作者： Ying Li Haiwei Xu Liping Fu Qingqing Shi Bo Jiang shujiang tu School of Chemistry and Chemical Engineering Laboratory of Green Synthetic Chemistry for Functional Materials Jiangsu Normal University Xuzhou Jiangsu 221116 China

Concise and efficient three-component domino [4＋ 1 ＋ 1] carbocyclization to highly substituted fluoren-9-one derivatives promoted by K2CO3 has been developed under microwave irradiation conditions. The direct bis-cyanation and aryl amination residing in fluoren-9-one framework were achieved in a one-pot operation. The reaction proceeds at fast rates and can be finished within 30 min, which makes workup convenient to give good to excellent chemical yields.

关键词： fluoren-9-one synthesis multicomponent reactions carbocyclization regioselectivity microwaveheating