Palladium-catalyzed [4+2] cycloaddition of amido-tethered allylic carbonates with oxazol-5-(4H)-ones: synthesis of piperidine-2,6-dione derivatives

被引：11

作者：

Wang, Lan ^{[1
,2
]}

Liu, Min ^{[1
,2
]}

Lu, Mengxi ^{[1
,2
]}

Wang, Bo ^{[1
,2
]}

Han, Qihuan ^{[1
,2
]}

Jin, Jingrong ^{[1
,2
]}

Yu, Songcheng ^{[3
]}

Wu, Yongjun ^{[3
]}

Guo, Hongchao ^{[1
,2
]}

机构：

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

[2] China Agr Univ, Innovat Ctr Pesticide Res, Beijing 100193, Peoples R China

[3] Zhengzhou Univ, Coll Publ Hlth, Zhengzhou 450001, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 03期

基金：

中国国家自然科学基金;

关键词：

METHYLIDENE-DELTA-VALEROLACTONES; VINYLETHYLENE CARBONATES; ANNULATION; ACCESS; CONSTRUCTION; LACTONES;

D O I：

10.1039/d2qo01783k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed [4 + 2] cycloaddition of amido-tethered allylic carbonates with oxazol-5-(4H)-ones proceeded smoothly under mild reaction conditions to give various piperidine derivatives in moderate to excellent yields. The reaction worked via aza-1,4-dipole from in situ deprotonation of amido-tethered allyl carbonates.

引用

页码：813 / 818

页数：6

共 38 条

[31] Palladium-catalyzed dearomatizative [2+2+1] carboannulation of 1,7-enynes with aryl diazonium salts and H2O: facile synthesis of spirocyclohexadienone-fused cyclopenta[c]quinolin-4(5H)-ones
Liu, Yu
Song, Ren-Jie
Li, Jin-Heng
CHEMICAL COMMUNICATIONS, 2017, 53 (61) : 8600 - 8603
[32] Palladium-Catalyzed Decarboxylative Synthesis of 5H-Benzo[4,5][1,3]oxazino[2,3-a]isoindole-5,11(6aH)-Diones using 2-Phenyl-4H-Benzo[d][1,3]oxazin-4-Ones and α-Oxo Carboxylic Acids
Lalji, Ram Sunil Kumar
Kumar, Prashant
Gupta, Mohit
Parmar, Virinder S.
Singh, Brajendra K.
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (03) : 552 - 560
[33] A new synthesis and 1,3-dipolar cycloaddition of C-aryl-N-(2,4-dibromophenyl)-nitrilimines with arylmaleimides leading to the synthesis of 1-(2′,4′-dibromophenyl)-3,5-diaryl-3a,4,6,6a-tetrahydro-1H,5H-pyrrolo[3,4-c] pyrazole-4,6-dione derivatives
Singal, KK
Singh, B
Singh, B
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1999, 38 (01): : 93 - 95
[34] PPh3-catalyzed knoevenagel condensation: A facile synthesis of 5-(1H-indol-3-yl)Methylene)-2, 2-Dimethyl-1, 3-Dioxane-4, 6-dione, and their N-alkyl derivatives by using peg-600 as the reaction medium
Venkatanarayana, Muvvala
Dubey, Pramod Kumar
HETEROATOM CHEMISTRY, 2012, 23 (01) : 41 - 48
[35] PRODUCTS FROM FURANS .6. SYNTHESIS OF DIHYDRO-2-DISUBSTITUTED-2H-PYRAN-3(4H)-ONES, TETRAHYDRO-3-(AMINOMETHYL)-2-(P-METHOXYPHENYL)-2-METHYL-2H-PYRAN-3-OL DERIVATIVES AND 6-(P-METHOXYPHENYL-6-METHYL-7-OXA-1,3-DIAZASPIRO[4,5]DECANE-2,4-DIONE
GEORGIADIS, MP
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (02) : 605 - 608
[36] Highly Regio- and Diastereoselective Synthesis of 6,7-Dihydro-4H-furo[3,4-c]pyran Derivatives through Pd-Catalyzed Formal (3+3) Allylic Cycloaddition of 2-Butene-1,4-diols with 2-(1-Alkynyl)-2-alken-1-ones
Yao, Tuanli
She, Jun-E
Li, Tao
Qin, Xiangyang
ORGANIC LETTERS, 2024, 26 (10) : 2018 - 2022
[37] Copper- and Palladium-Catalyzed Cross-Coupling Reactions for the Synthesis of N-Fused Benzo[4,5]imidazo[2,1-b]thiazole Derivatives via Substituted trans-1,2-Diiodoalkenes, 1H-Benzo[d]imidazole-2-thiols, and Halobenzenes
Shen, Guodong
Yang, Bingchuan
Huang, Xianqiang
Hou, Yaxin
Gao, Huan
Cui, Jichun
Cui, Chuansheng
Zhang, Tongxin
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (07): : 3798 - 3805
[38] 1,3-Dipolar cycloaddition reactions of substituted open-chain conjugated azomethine N-oxides with substituted N-arylmaleimides leading to the synthesis of new stereoisomeric 2,5-diaryl-3-(o-nitro)-styryl-4H-2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6-dione derivatives
Singal, KK
Singh, B
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1999, 38 (03): : 292 - 296

← 1 2 3 4 →