Synthesis of novel spirocyclic 2-oxindole tethered to 2′-(3-(furan-2-yl)-1H-pyrazole-4-carbonyl)-hexahydropyrrolizine via 1,3-dipolar cycloaddition of the chalcone with azomethine ylide: Reaction of pyrazolyl-enaminone towards some heteroaromatic amines

被引：7

作者：

Saleh, Fatma M. ^{[1
]}

Hassaneen, Hamdi M. ^{[1
]}

Abdelhamid, Ismail A. ^{[1
]}

Teleb, Mohamed A. Mohamed ^{[1
]}

机构：

[1] Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt

来源：

TETRAHEDRON LETTERS | 2024年 / 137卷

关键词：

Chalcone; Spirooxindole; Hexahydropyrrolizine; Enaminone; 1,2,4]Triazolo[1,5-a]pyrimidine; Benzo[4,5]imidazo[1,2-a]pyrimidine; ORGANIC-SYNTHESIS; DERIVATIVES; REGIOSELECTIVITY; AZAENAMINES; PYRIDAZINES; CHITOSAN; HALIDES; ROUTE; ARENE;

D O I：

10.1016/j.tetlet.2024.154957

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new series of 3-(furan-2-yl)pyrazole tethered to hexahydrospiro[indoline-3,3 '-pyrrolizin]-2-one via carbonyl moiety were prepared via a facile intermolecular 1,3 -dipolar cycloaddition of the chalcone with azomethine ylide intermediate (generated by the decarboxylative condensation of isatin with L-proline). A new [1,2,4]triazolo[1,5a]pyrimidines and benzo[4,5]imidazo[1,2-a]pyrimidines tethered to furan-2-yl-1H-pyrazole moiety have been synthesized via the respective reaction of enaminone with 3-amino-[1,2,4]triazole and benzo[d]imidazol-2- amine. The regio orientation was confirmed based on spectral data.

引用

页数：5

共 7 条

[1] Study on Regio- and Diastereoselectivity of the 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide with 2-(Benzo[d]thiazol-2-yl)-3-(aryl)acrylonitrile: Synthesis, Spectroscopic, and Computational Approach
Hussein, Essam M.
Moussa, Ziad
Al-Fahemi, Jabir H.
Al-Rooqi, Munirah M.
Obaid, Rami J.
Malik, M. Shaheer
Abd-El-Aziz, Alaa S.
Ahmed, Saleh A.
ACS OMEGA, 2024, 9 (22): : 23802 - 23821
[2] An Efficient Synthesis of 3-(1H-Tetrazol-5-yl)coumarins (=3-(1H-Tetrazol-5-yl)-2H-1-benzopyran-2-ones) via Domino Knoevenagel Condensation, Pinner Reaction, and 1,3-Dipolar Cycloaddition in Water
Tisseh, Zeinab Noroozi
Dabiri, Minoo
Bazgir, Ayoob
HELVETICA CHIMICA ACTA, 2012, 95 (09) : 1600 - 1604
[3] One-pot Regioselective Synthesis of Novel 1-N-Methyl-spiro[2,3′]oxindole-spiro[3,3"]-1"-N-arylpyrrolidine-2",5"-dione-4-arylpyrrolidines through Multicomponent 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide
Kaur, Anjandeep
Kaur, Manpreet
Singh, Baldev
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (03) : 827 - 833
[4] Regio- and stereoselective synthesis of novel spiropyrrolidines through 1,3-dipolar cycloaddition reactions of azomethine ylides and 2-styrylquinazolin-4(3H)-ones
Maurya, Ram Awatar
Nayak, Ranjita
Reddy, Chada Narsimha
Kapure, Jeevak Sopanrao
Nanubolu, Jagadeesh Babu
Singarapu, Kiran Kumar
Ajitha, M.
Kamal, Ahmed
RSC ADVANCES, 2014, 4 (61): : 32303 - 32311
[5] Synthesis of Novel 1-(1,5-Diaryl-1,10b-Dihydropyrrolo- [1,2-A][1,2,4]Triazolo[3,4-C]Pyrazin-3-Yl)Ethanones Via 1,3-Dipolar Cycloaddition of Nitrilimine
Huang, Yulin
Ren, Demin
Yu, Xianyong
Zeng, Ju-Lan
Li, Xiaofang
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (01) : 84 - 87
[6] One-pot synthesis of 3-(furan-2-yl)-4H-chromen-4-ones from 1-(2-hydroxyphenyl)butane-1,3-diones and 2,5-dimethoxy-2,5-dihydrofuran catalyzed via K10 montmorillonite under solvent-free conditions
Han, Jie
Wang, Tao
Feng, Siqi
Li, Chenchen
Zhang, Zunting
GREEN CHEMISTRY, 2016, 18 (14) : 4092 - 4097
[7] Synthesis of 2′,3′,4′-triaryl-5,6-dihydro-8H-spiro[indolizine-7,5′-isoxazolidin]-8-ones via 1,3-dipolar cycloaddition reaction involving (Z)-C-aryl-N-phenylnitrones
Li, Youfeng
Tang, Jin
Li, Xiaofang
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (08) : 1062 - 1066

← 1 →