Morita-Baylis-Hillman reaction of pyridine-2, 3, and 4-carboxaldehydes and N-methyl isatin with mono and diacrylates: synthesis of highly functionalized pyridine ligands and isatin derivatives

被引：10

作者：

Malini, Kodi ^{[1
]}

Periyaraja, Somasundharam ^{[1
]}

Shanmugam, Ponnusamy ^{[1
]}

机构：

[1] Cent Leather Res Inst, CSIR, Div Organ Chem, Madras 600020, Tamil Nadu, India

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 36期

关键词：

MBH reaction; Pyridine; Isatin; Pyridine-N-oxide; Spiro pyrrolidine oxindole; ADDUCTS;

D O I：

10.1016/j.tetlet.2015.07.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Morita-Baylis-Hillman reaction of pyridine-2, 3, and 4-carboxaldehydes and N-methyl isatin with less explored activated alkenes such as 1,6-hexanediol diacrylate (HDDA) and acrylates of lauryl and isoboronyl has been carried out to provide diversely functionalized mono and bis MBH adduct of pyridine aldehydes and isatin in very good yields. Synthetic use of MBH adducts thus obtained has been demonstrated by preparing pyridine-N-oxide derivatives and [3+2]-azomethine ylide cycloaddition products. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5123 / 5127

页数：5

共 7 条

[1] Synthesis of Functionalized 1,2,3-Triazole Derivatives of 2-Indolones from Morita-Baylis-Hillman Adducts of Isatin via "Click Chemistry"
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[2] Nucleophilic substitution reaction of Morita-Baylis-Hillman adducts of isatin with X, S, N, and O-nucleophiles: a facile and efficient synthesis of highly functionalized tetrasubstituted alkene appended oxindoles
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[3] Pyridine Core Activation via 1,5-Electrocyclization of Vinyl Pyridinium Ylides Generated from Bromo Isomerized Morita-Baylis-Hillman Adduct of Isatin and Pyridine: Synthesis of 3-Spirodihydroindolizine Oxindoles
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ORGANIC LETTERS, 2010, 12 (09) : 2108 - 2111
[4] A novel Mgl2 mediated unusual dimerization-spirocyclopropanation of bromo isomerised Morita-Baylis-Hillman adduct of isatin: a facile synthesis of 3-spirocyclopropane-2-oxindole derivatives
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[6] Synthesis of functionalized spiro[indanone-benzazepine] scaffolds via [4+3] annulation reaction of N-(o-chloromethyl)aryl amides with ninhydrin-derived Morita-Baylis-Hillman carbonates
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[7] Synthesis of Furo[3,2-c]pyridine-2,4-dione Derivatives by the Reaction of 1-Methyl-4-phenyl-5,6-dihydropyridin-2(1H)-one with Carboxylic Acids in the Presence of Manganese Triacetate
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