A novel and facile synthesis of 2-oxo-1,2-dihydropyridine-fused 1,3-diazaheterocycles via heterocyclic ketene aminals and Konevenagel adducts formed by phthalic anhydride and ethyl cyanacetate

A novel and facile synthesis of 2-oxo-1,2-dihydropyridine-fused 1,3-diazaheterocycles via heterocyclic ketene aminals and Konevenagel adducts formed by phthalic anhydride and ethyl cyanacetate

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摘要 An efficient synthetic pathway to 2-oxo-1,2-dihydropyridine-fused 1,3-diaza heterocycles from heterocyclic ketene aminals,phathalic anhydride and ethyl cyanacetate was established.This protocol involved aza-ene reaction/imine-enamine tautomerization/enamine-ester exchange/ring-opening reaction sequence. An efficient synthetic pathway to 2-oxo-1,2-dihydropyridine-fused 1,3-diaza heterocycles from heterocyclic ketene aminals,phathalic anhydride and ethyl cyanacetate was established.This protocol involved aza-ene reaction/imine-enamine tautomerization/enamine-ester exchange/ring-opening reaction sequence.

作者 Min-Ming Zou Feng-Juan Zhu Xue Tian Li-Ping Ren Xu-Sheng Shao Zhong Li

机构地区 Shanghai Key Laboratory of Chemical Biology

出处《Chinese Chemical Letters》 SCIE CAS CSCD 2014年第12期1515-1519,共5页 中国化学快报（英文版）

基金 financial supported by National Natural Science Foundation of China(No.21372079) National High Technology Research Development Program of China(863 Program,No. 2011AA10A207) Shanghai Pujiang Program(No.14PJD012) Key Projects in the National Science & Technology Pillar Program(No. 2011BAE06B05) the Fundamental Research Funds for the Central Universities partly supported by Australia DC Foundation

关键词 Heterocyclic ketene aminals 2-Oxo-1 2-dihydropyridine 1 3-Diazaheterocycle Synthesis Heterocyclic ketene aminals 2-Oxo-1,2-dihydropyridine 1,3-Diazaheterocycle Synthesis

分类号 O626 [理学—有机化学] S816.7 [农业科学—饲料科学]

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1Nan-Yang Chen,Li-Ping Ren,Min-Ming Zou,Zhi-Ping Xu,Xu-Sheng Shao,Xiao-Yong Xu,Zhong Li.Design,synthesis and insecticidal activity of spiro heterocycle containing neonicotinoid analogs[J].Chinese Chemical Letters,2014,25(2):197-200. 被引量：5

二级参考文献26

1R. Rios, Enantioselective methodologies for the synthesis of spiro compounds, Chem. Soc. Rev. 41 (2012) 1060-1074.
2T. Jin, M. Himuro, Y. Yamamoto, Triflic acid catalyzed synthesis of spirocycles via acetylene cations, Angew. Chem. Int. Ed. 48 (2009) 5893-5896.
3G.S. Singh, Z.Y. Desta, lsatins as privileged molecules in design and synthesis of spiro-fused cyclic frameworks, Chem. Rev. 112 (2012) 6104-6155.
4H. Diirr, R. Gleiter, Spiroconjugation, Angew. Chem. Int. Ed. 17 (1978) 559-569.
5B. Gleiter, H. Hoffmann, H. Irngartinger, M. Nixdorf, Donor-acceptor spiro-com- pounds-syntheses, structures and electronic properties, Chem. Ber. 127 (1994) 2215-2224.
6J. Sun, Y.J. Xie, C.G. Yan, Construction of dispirocyclopentanebisoxindoles via self- domino michael-aldol reactions of 3-phenacylideneoxindoles, J. Org. Chem. 78 (2013) 8354-8365.
7K. Mural, H. Komatsu, R. Nagao, H. Fujioka, Oxidative rearrangement of spiro cyclobutane cyclic aminals: efficient construction of bicyclic amidines, Org. Lett. 14 (2012) 772-775.
8W.Y. Xu, Y.M. Jia, J.K. Yang, Z.T. Huang, C.Y. Yu, Reactions of heterocyclic detene aminals with 2-[3-oxoisobenzofuran-l(3H)-ylidenne]malononitrile: synthesis of novel polyfunctionalized lA-dihydropyridine-fused 1,3-diazaheterocycles, Syn- lett 11 (2010) 1682-1684.
9F. Shi, G.J. Xing, R.Y. Zhu, W. Tan, S.J. Tu, A catalytic asymmetric isatin-involved povarov reaction: diastereo- and enantioselective construction of spiro[indolin- 3,2'-quinoline] scaffold, Org. Lett. 15 (2013) 1128-1131.
10S. Pal, M.N. Khan, S. Karamthulla, S.J. Abbas, L.H. Choudhury, One pot four- component reaction for the efficient synthesis of spiro[indoline-3,4'-pyr- ano[2,3-c]pyrazole]-3'-carboxylate derivatives, Tetrahedron Lett. 54 (2013) 5434-5440.

共引文献4

1Shao-Hua Liu,Wei Peng,Yan-Yan Qu,Dan Xu,Hong-Yue Li,Dun-Lun Song,Hong-Xia Duan,Xin-Ling Yang.Synthesis, insecticidal activity and molecular docking study of clothianidin analogues with hydrazide group[J].Chinese Chemical Letters,2014,25(7):1017-1020. 被引量：2
2Xuan-Qi Liu,Ya-Qin Liu,Xu-Sheng Shao,Zhi-Ping Xu,Xiao-Yong Xu,Zhong Li.Synthesis and insecticidal evaluation of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives[J].Chinese Chemical Letters,2016,27(1):7-10.
3Ping Wu,Hong Gao,Jing Sun,Chao-Guo Yan.1,3-Dipolar cycloaddition reaction for diastereoselective synthesis of functionalized dihydrospiro[indoline-3,2'-pyrroles][J].Chinese Chemical Letters,2017,28(2):329-332. 被引量：1
4邵旭升,杜少卿,李忠,钱旭红.中国绿色农药的研究和发展[J].世界农药,2020,42(4):16-24. 被引量：21

1WANG Meixiang and HUANG Zhitang(Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China).Advances in heterocyclic ketene aminals[J].Progress in Natural Science:Materials International,2002,12(4):249-257. 被引量：2
2Qiang YANG,Zhan Jiang LI,Zhi Tang HUANG (Institute of Chemistry. The Chinese Academy of Sciences, Beijing 100080).Synthesis of O-Glycosides of Heteroatom Aroyl-Substituted Heterocyclic Ketene Aminals[J].Chinese Chemical Letters,1999,10(8):661-664.
3Zhan Jiang LI,Li Ben WANG,and Zhi Tang HUANG(Institute of Chemistry. Academia Sinica. Beijing 100080).A　FACILE　METHOD　FOR　THE　O－GLYCOSIDATION　OF　BENZOYL　SUBSTITUTED　HETEROCYCLIC　KETENE　AMINALS[J].Chinese Chemical Letters,1995,6(3):185-188.
4Jing LI, You Cheng LIU, Jin Gen DENG (Department of Chemistry. University of Science and Technology of China, Hefei 230026,Chengdu Institute of Organic Chemistry. Chinese Academy of Sciences. Chengdu 610041,National Laboratory of Applied Organic Chemis.An Improved and Efficient Preparation of the Chiral NAD(P)H Model (S_s)-1-Benzy1-3-(p-tolylsulfinyl)-1,4-dihydropyridine[J].Chinese Chemical Letters,2000,11(3):209-212.
5ZHU Yi-qiang,TANG Hui-tong,ZHANG Pang.Formation of Pyrrolidin-1-ylcyclopentadienes via Cyclization of Alkyl 2-Dimethoxyacetyl-and 2-Ethoxalyl-4-oxopentanoates[J].Chemical Research in Chinese Universities,1998,14(2):23-29.
6Zhi Tang HUANG,Jian Chao,WANG and Li Ben WANG Institute of Chemistry, Academia Sinica. Beijing, 100080.Absrtact: Heterocyclic ketene aminals 1 or 2 react with dichlorocarbene to give the formyl substituted heterocylic ketene aminals 3 or 4through the ca.REACTION OF HETEROCYCLIC KETENE AMINALS WITH DICHLOROCARBENE[J].Chinese Chemical Letters,1995,6(1):5-8. 被引量：1
7徐占辉,黄志镗.O-Maltosylation of Heterocyclic Ketene Aminals[J].Chinese Journal of Chemistry,2002,20(10):1065-1069.
8佘小平,王晓明,杨建雄,黄维玉,桂美祥.激动素对韭菜叶片衰老的影响与活性氧代谢的关系[J].西北植物学报,1992,12(4):282-286. 被引量：2
9杨奇超,王玉芳,张保集,张明杰.Direct N-Arylation of Azaheterocycles with Aryl Halides under Ligand-free Condition[J].Chinese Journal of Chemistry,2012,30(10):2389-2393.
10Peng-Zhong Chen,Hai-Rong Zheng,Li-Ya Niu,Yu-Zhe Chen,Li-Zhu Wu,Chen-Ho Tung,Qing-Zheng Yang.A BODIPY analogue from the tautomerization of sodium 3-oxide BODIPY[J].Chinese Chemical Letters,2015,26(6):631-635. 被引量：1

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2014年第12期

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A novel and facile synthesis of 2-oxo-1,2-dihydropyridine-fused 1,3-diazaheterocycles via heterocyclic ketene aminals and Konevenagel adducts formed by phthalic anhydride and ethyl cyanacetate

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