Regio- and stereoselective synthesis of new spiro-isoxazolidines via 1,3-dipolar cycloaddition

被引：8

作者：

Jegham, Nafaa ^{[1
]}

Bahi, Amira ^{[1
]}

El Guesmi, Nizar ^{[2
,3
]}

Kacem, Yakdhane ^{[1
]}

Ben Hassine, Bechir ^{[1
]}

机构：

[1] Fac Sci Monastir, Lab Synth Organ Asymetr & Catalyse Homogene 01UR1, Ave Environm, Monastir 5000, Tunisia

[2] Fac Sci Monastir, Dept Chim, Ave Environm, Monastir 5000, Tunisia

[3] Umm Alqura Univ, Fac Appl Sci, Dept Chem, POB 9569, Mecca, Saudi Arabia

来源：

ARABIAN JOURNAL OF CHEMISTRY | 2017年 / 10卷

关键词：

1,3-Dipolar cycloaddition; Isoquinolinediones; Nitrones; Regiochemistry; Stereoselective; Spiroisoxazolidines; ARYL-N-PHENYLNITRONES; ARYLNITRILE OXIDES; NITRONES;

D O I：

10.1016/j.arabjc.2014.05.028

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New spiro-isoquinolinediones were prepared by regio- and stereoselective 1,3-dipolar cycloaddition of (E)-4-arylidene-N-methyl-isoquinoline-1,3-dione derivatives 1a-d with C-aryl-N-phenylnitrones 2e-g. NMR studies confirmed that only one regioisomer was formed selectively in the majority of cases. Regioselectivity of the reaction was established by H-1 and C-13 NMR assignments. The stereochemistry of spirannic compounds 3a-l and 4a-c has been corroborated by means of DFT calculations. The structures of all the products were characterized thoroughly by NMR and elemental analyses. (C) 2014 King Saud University. Production and hosting by Elsevier B.V.

引用

页码：S3889 / S3894

页数：6

共 50 条

[31] Four-Component Regio- and Diastereoselective Synthesis of Pyrrolizidines Incorporating Spiro-Oxindole/Indanedione via 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylides
Alizadeh, Abdolali
Roosta, Atefeh
Halvagar, Mohammadreza
CHEMISTRYSELECT, 2019, 4 (01): : 71 - 74
[32] STEREOSELECTIVE SYNTHESIS OF (+)-TESTOSTERONE VIA INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDE
IHARA, M
TOKUNAGA, Y
TANIGUCHI, N
FUKUMOTO, K
TETRAHEDRON, 1991, 47 (33) : 6635 - 6648
[33] Stereoselective synthesis of spiro and condensed pyrazolines of steroidal α,β-unsaturated ketones and nitrilimines by 1,3-dipolar cycloaddition
Mernyak, Erzsebet
Koma, Eszter
Hetenyi, Anasztazia
Mark, Laszlo
Schneider, Gyula
Woelfling, Janos
STEROIDS, 2009, 74 (06) : 520 - 525
[34] Regio- and diastereoselective 1,3-dipolar cycloaddition of imidazoline 3-oxides to styrene
Coskun, N
Ay, M
HETEROCYCLES, 1998, 48 (03) : 537 - 544
[35] Synthesis of celecoxib via 1,3-dipolar cycloaddition
Oh, Lynette M.
TETRAHEDRON LETTERS, 2006, 47 (45) : 7943 - 7946
[36] An expedient regio and diastereoselective synthesis of novel spiropyrrolidinylindenoquinoxalines via 1,3-dipolar cycloaddition reaction
Reddy, Marri Sameer
Chowhan, L. Raju
Kumar, Nandigama Satish
Ramesh, Pambala
Mukkamala, Saratchandra Babu
TETRAHEDRON LETTERS, 2018, 59 (14) : 1366 - 1371
[37] Synthesis of new η6-(arene) chromium tricarbonyl complexes of isoxazolidines by 1,3-dipolar cycloaddition
Artemov, A. N.
Sazonova, E. V.
Mavrina, E. A.
Zarovkina, N. Yu.
RUSSIAN CHEMICAL BULLETIN, 2012, 61 (11) : 2076 - 2081
[38] Synthesis of New Spiro Isoxazoline-Pyrrolizinone Derivatives via 1,3-Dipolar Cycloaddition of Nitrile Oxide
Li, X.
Yi, R.
Liu, B.
Zheng, A.
Yu, X.
Yi, P.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (01) : 274 - 276
[39] A Facile Regio- and Stereoselective Synthesis and Cholinesterase Inhibitory Activity of New Oxobenzothiophene Grafted Spiropyrrolidine/Pyrrolizidine Hybrids Employing Multicomponent 1,3-Dipolar Cycloaddition Methodology
Raju, Rajesh
Mani, Suresh
Arumugam, Natarajan
Almansour, Abdulrahman I.
Kumar, Raju Suresh
Premnath, Dhanaraj
Perumal, Karthikeyan
CHEMISTRYSELECT, 2023, 8 (32):
[40] Synthesis of Novel Spiro Indolizidine Derivatives via 1,3-Dipolar Cycloaddition of Azomethine Ylide
Li, Xiaofang
Yi, Rongqiong
Liu, Bin
Li, Zhikui
Yu, Xianyong
Yi, Pinggui
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (12) : 2309 - 2314

← 1 2 3 4 5 →