A simple and efficient method for the synthesis of Erlenmeyer azlactones

被引：65

作者：

Conway, Philip A. ^{[1
]}

Devine, Kevin ^{[1
]}

Paradisi, Francesca ^{[1
]}

机构：

[1] Univ Coll Dublin, Sch Chem & Chem Biol, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

TETRAHEDRON | 2009年 / 65卷 / 15期

基金：

爱尔兰科学基金会;

关键词：

Aromatic azlactones; Aliphatic azlactones; Solid-phase catalysis; ALIPHATIC-ALDEHYDES;

D O I：

10.1016/j.tet.2009.02.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have recently developed a novel and efficient method for synthesising Erlenmeyer azlactones under mild and rapid conditions. The reaction is performed by reacting 2-phenyl-5-oxazolone with an aldehyde in dichloromethane using alumina as a catalyst. The materials react instantly at room temperature, negating the need for high temperatures and long reaction times. We have successfully used this method for both aliphatic, aromatic and heteroaromatic aldehydes, synthesising previously unmade Erlenmeyer azlactones in moderate to high yields. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2935 / 2938

页数：4

共 50 条

[1] Solid support Erlenmeyer synthesis of azlactones using microwaves
Mogilaiah, K
Prashanthi, M
Reddy, CS
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2003, 42 (09): : 2126 - 2128
[2] SYNTHESIS OF ERLENMEYER AZLACTONES USING ARYLSULPHONYL CHLORIDE AS CYCLOCONDENSING AGENT
Goswami, Limi
Tripathy, Pradeep K.
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 24 (03) : 281 - 282
[3] Synthesis, bioassay, crystal structure and ab initio studies of Erlenmeyer azlactones
Parveen, Mehtab
Ali, Akhtar
Ahmed, Sarfaraz
Malla, Ali Mohammed
Alam, Mahboob
Pereira Silva, P. S.
Silva, Manuela Ramos
Lee, Dong-Ung
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2013, 104 : 538 - 545
[4] SYNTHESIS OF ERLENMEYER-PLOCHL AZLACTONES PROMOTED BY 5-SULFOSALICYLIC ACID
Kiyani, Hamzeh
Aslanpour, Shiva
HETEROCYCLES, 2017, 94 (07) : 1314 - 1321
[5] Bismuth (III) acetate: A new catalyst for preparation of azlactones via the Erlenmeyer synthesis
Monk, KA
Sarapa, D
Mohan, RS
SYNTHETIC COMMUNICATIONS, 2000, 30 (17) : 3167 - 3170
[6] Alum an Efficient Catalyst for Erlenmeyer Synthesis
Madje, Balaji R.
Ubale, Milind B.
Bharad, Jagdish V.
Shingare, Murlidhar S.
SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE, 2010, 63 : 158 - 161
[7] Erlenmeyer synthesis for azlactones catalyzed by ytterbium(III) triflate under solvent-free conditions
Yu, Chuanming
Zhou, Baocheng
Su, Weike
Xu, Zhenyuan
SYNTHETIC COMMUNICATIONS, 2006, 36 (22) : 3447 - 3453
[8] Ammonium metavanadate an efficient catalyst for Erlenmeyer synthesis
Madje, Balaji
Ubale, Milind
Bharad, Jagdish
Shingare, Murlidhar
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2012, 89 (09) : 1295 - 1299
[9] SYNTHESIS OF ERLENMEYER-PIOCHL AZLACTONES PROMOTED BY 5-SULFOSALICYLIC ACID (vol 94, pg 1314, 2017)
Aslanpour, Shiva
Kiyani, Hamzeh
HETEROCYCLES, 2019, 98 (04) : 619 - 619
[10] Base Induced Condensation of Malononitrile with Erlenmeyer Azlactones: An Unexpected Synthesis of Multi-Substituted Δ2-Pyrrolines and Their Cytotoxicity
Anil, Seegehalli M.
Sudhanva, Muddenahalli S.
Swaroop, Toreshettahally R.
Vinayaka, Ajjampura C.
Rajeev, Narasimhamurthy
Kiran, Kuppalli R.
Shobith, Rangappa
Sadashiva, Maralinganadoddi P.
CHEMISTRY & BIODIVERSITY, 2020, 17 (05)

← 1 2 3 4 5 →