Iron(III) Chloride/L-Proline as an Efficient Catalyst for the Synthesis of 3-Substituted 1,2,4-Oxadiazoles from Amidoximes and Triethyl Orthoformate

被引：10

作者：

Kaboudin, Babak ^{[1
]}

Kazemi, Foad ^{[1
]}

Pirouz, Maryam ^{[1
]}

Khoshkhoo, Aysan Baharian ^{[1
]}

Kato, Jun-Ya ^{[2
]}

Yokomatsu, Tsutomu ^{[2
]}

机构：

[1] IASBS, Dept Chem, Zanjan 4513766731, Iran

[2] Tokyo Univ Pharm & Life Sci, Sch Pharm, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 20期

关键词：

1,2,4-oxadiazoles; iron(III) chloride; L-proline; amidoximes; triethyl orthoformate; OXADIAZOLE SYNTHESIS; DERIVATIVES; DISCOVERY; POTENT; INHIBITORS; CHEMISTRY; NITRILES; FLUORIDE; AGONISTS; REAGENT;

D O I：

10.1055/s-0035-1562431

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, facile, and efficient method is presented for the synthesis of 3-substituted 1,2,4-oxadiazoles from amidoximes and triethyl orthoformate. The procedure employs an iron(III) chloride/L-proline catalytic system and the 3-substituted 1,2,4-oxadiazole products are obtained in moderate to good yields.

引用

页码：3597 / 3602

页数：6

共 50 条

[1] 2 NOVEL SYNTHESES OF SUBSTITUTED 1,2,4-OXADIAZOLES FROM AMIDOXIMES
STEGLICH, W
VANREE, T
SYNTHETIC COMMUNICATIONS, 1982, 12 (06) : 457 - 461
[2] PTSA-ZnCl2: An Efficient Catalyst for the Synthesis of 1,2,4-Oxadiazoles from Amidoximes and Organic Nitriles
Augustine, John Kallikat
Akabote, Vani
Hegde, Shrivatsa Ganapati
Alagarsamy, Padma
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15): : 5640 - 5643
[3] Synthesis of substituted 1,2,4-oxadiazoles from substituted acid chlorides and amidoximes under mild conditions
Bora, Rajesh O.
Farooqui, Mazahar
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (03) : 645 - 649
[4] A CONVENIENT SYNTHESIS OF 3-SUBSTITUTED 5-GUANIDINO-1,2,4-OXADIAZOLES
YAROVENKO, VN
SHIRINYAN, YZ
ZAVARZIN, IV
KRAYUSHKIN, MM
RUSSIAN CHEMICAL BULLETIN, 1994, 43 (01) : 114 - 117
[5] Electrochemical synthesis of 1,2,4-oxadiazoles from amidoximes through dehydrogenative cyclization
Jiang, Chan
Li, Mingfang
Xu, Leitao
Yi, Yangjie
Ye, Jiao
Hu, Aixi
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (48) : 10611 - 10616
[6] Microwave assisted synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from substituted amidoximes and benzoyl cyanides
Kandre, Shivaji
Bhagat, Pundlik Rambhau
Sharma, Rajiv
Gupte, Amol
TETRAHEDRON LETTERS, 2013, 54 (27) : 3526 - 3529
[7] Synthesis of 3-substituted Coumarins: An Efficient Green Approach Using L-proline as Catalyst in Triethanolamine Medium
Srikrishna, Devulapally
Tasqeeruddin, Syed
Dubey, Pramod Kumar
LETTERS IN ORGANIC CHEMISTRY, 2014, 11 (08) : 556 - 563
[8] SYNTHESIS AND PRELIMINARY PHARMACOLOGICAL STUDIES OF SOME 3-SUBSTITUTED 5-AMINO-1,2,4-OXADIAZOLES
CAVALLERI, B
VOLPE, G
ROSSELLIDELTURCO, B
DIENA, A
FARMACO-EDIZIONE SCIENTIFICA, 1976, 31 (06): : 393 - 402
[9] Synthesis and anticancer activity of novel 5-(indole-2-yl)-3-substituted 1,2,4-oxadiazoles
Wang, Peng
Liu, Jianzhen
Xing, Hualu
Liu, Yang
Xie, Wencheng
Zhao, Guisen
DRUG DISCOVERIES AND THERAPEUTICS, 2012, 6 (03): : 133 - 139
[10] REACTION OF 1,3,5-TRIAZINE WITH AROMATIC NITRILE OXIDES - NEW SYNTHESIS OF 3-SUBSTITUTED 1,2,4-OXADIAZOLES
KURABAYASHI, M
GRUNDMANN, C
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (05) : 1484 - 1486

← 1 2 3 4 5 →