[3+2] Cycloaddition of Methylenedihydrobenzofurandiones and Nitrilimines: Synthesis of Sipropyrazole Compounds

被引：2

作者：

Shi, Wangyu ^{[1
]}

Xu, Jiaqing ^{[1
]}

Mao, Biming ^{[1
]}

Jia, Hao ^{[1
]}

Huang, Jiaxing ^{[1
]}

Guo, Hongchao ^{[1
]}

机构：

[1] China Agr Univ, Coll Sci, Dept Chem, Beijing 100193, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 40卷 / 03期

基金：

中国国家自然科学基金;

关键词：

cycloaddition; nitrilimine; spirocyclic compound; pyrazole; BAYLIS-HILLMAN CARBONATES; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITIONS; C; N-CYCLIC AZOMETHINE IMINES; NITRILE IMINES; 1.3-DIPOLARE ADDITIONEN; INSECTICIDAL ACTIVITIES; BIOLOGICAL EVALUATION; FACILE SYNTHESIS; PYRAZOLE AMIDES; 4+3 ANNULATION;

D O I：

10.6023/cjoc201907030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The [3+2] cycloaddition of methylenedihydrobenzofurandiones and nitrilimines worked efficiently in CHCl3 at room temperature in the presence of Et3N, producing biologically interesting spirocyclic pyrazole derivatives in high yield (78%similar to 94%) with excellent diastereoselectivity.

引用

页码：756 / 762

页数：7

共 79 条

[1] Simple access to spirooxadiazole compounds containing a quinoxaline moiety using a nitrile imine intermediate generated in situ
Alizadeh, Abdolali
Moafi, Leila
[J]. HETEROCYCLIC COMMUNICATIONS, 2017, 23 (05) : 375 - 378
[2] Convenient One-Pot Synthesis of Spirooxindole Derivatives Containing a 1,3,4-Thiadiazine Scaffold
Alizadeh, Abdolali
Moafi, Leila
[J]. SYNLETT, 2016, 27 (12) : 1828 - 1831
[3] A new route for the synthesis of 1,3,4-trisubstituted pyrazolo[4,3-c] quinolines via a multicomponent reaction
Alizadeh, Abdolali
Moafi, Leila
Ghanbaripour, Rashid
Abadi, Marziyeh Hossein
Zhu, Zhe
Kubicki, Maciej
[J]. TETRAHEDRON, 2015, 71 (21) : 3495 - 3499
[4] FREE-RADICAL CYCLIZATIONS LEADING TO NITROGEN-HETEROCYCLES .2. 2-PHENYLPYRAZOLIDIN-3-ONES VIA TRIBUTYLTIN HYDRIDE REACTION WITH ALPHA-BROMOACYLATED PHENYLHYDRAZONES
BELLETIRE, JL
HAGEDORN, CE
HO, DM
KRAUSE, J
[J]. TETRAHEDRON LETTERS, 1993, 34 (05) : 797 - 800
[5] A REVIEW ON RECENT DEVELOPMENT OF PYRAZOLINE AS A PHARMOCOLOGICALLY ACTIVE MOLECULE
Bhutani, Rubina
Pathak, Dharam Pal
Husain, Asif
Kapoor, Garima
Kant, Ravi
[J]. INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2015, 6 (10): : 4113 - 4128
[6] Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides
Blackburn, J.
Molyneux, G.
Pitard, A.
Rice, C. R.
Page, M. I.
Afshinjavid, S.
Javid, F. A.
Coles, S. J.
Horton, P. N.
Hemming, K.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (06) : 2134 - 2144
[7] UNUSUAL REACTION OF 4-MERCAPTO-1,2,3-BENZOTRIAZINE WITH N-(2,4-DIBROMOPHENYL) BENZOHYDRAZONYL BROMIDE
CALLAGHAN, PD
ELLIOTT, AJ
GIBSON, MS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (14): : 2131 - 2131
[8] Synthesis and tautomerism of spiro-pyrazolines
Dadiboyena, Sureshbabu
Valente, Edward J.
Hamme, Ashton T., II
[J]. TETRAHEDRON LETTERS, 2014, 55 (14) : 2208 - 2211
[9] Synthesis and Biological Activities of Novel Pyrazole Amide Derivatives Containing Substituted Isoxazole Group
Dai, Hong
Yao, Wei
Ye, Linyu
Fang, Yuan
Shi, Yujun
Song, Chan
Li, Chunjian
Shi, Jian
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (08) : 2165 - 2171
[10] Synthesis and Bioactivities of Novel Pyrazole Oxime Ester Derivatives Containing Pyridyl Moiety
Dai, Hong
Chen, Jia
Hong, Yu
Yuan, Binying
Fan, Chongguang
Ma, Ruiyuan
Liang, Zhipeng
Shi, Jian
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (06) : 1542 - 1547

← 1 2 3 4 5 6 7 8 →