Microwave assisted IMDAF# reaction: Microwave irradiation applied with success to cycloaddition reaction of N-propargyl-N-p-tolyl-N-2-furfurylamines

Mance, Ana Dunja; Jakopcic, K.

doi:10.1007/s11030-005-3434-8

Cited by 10 publications

(3 citation statements)

References 11 publications

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“…Our theoretical studies revealed that the increased reactivity of ortho -substituted compounds is mainly due to a steric effect, which destabilizes the minimum conformation of the reactant compared to the active conformations . In order to improve the reaction with respect to less reactive starting materials, we have now turned to microwave chemistry, which to some extent has been applied in IMDAF reactions before . We herein report that not only was the reactivity in the Diels–Alder reaction greatly improved, also it is possible to carry out one-pot syntheses of dihydrophenanthridine and aza analogues, if the reaction is carried out in the presence of acid.…”

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confidence: 94%

Synthesis of Phenanthridine Derivatives by Microwave-Mediated Cyclization of o-Furyl(allylamino)arenes

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Gundersen

2013

J. Org. Chem.

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A novel and efficient synthesis of phenanthridines and aza analogues is reported. The key step is a microwave-mediated intramolecular Diels-Alder cyclization of o-furyl(allylamino)arenes. In the presence of a catalytic amount of acid, the DA-adduct reacts further to give the dihydrophenanthridines, which easily can be oxidized to fully aromatic compounds by air in the presence of UV light or by DDQ.

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confidence: 94%

Synthesis of Phenanthridine Derivatives by Microwave-Mediated Cyclization of o-Furyl(allylamino)arenes

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Gundersen

2013

J. Org. Chem.

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“…Synthetic chemists are still trying to make the conditions for Diels–Alder reactions more environmentally friendly [ 48 – 58 ]. However, the number and variety of substrates in these studies is often limited, deep eutectic solvents are required and it is difficult to achieve both satisfactory product yields and the desired stereoselectivity [ 59 – 61 ]. The viscous nature of the aminofuranes usually requires the use of toxic solvents such as toluene, and in some studies, solvents such as DMSO, which are difficult to remove from the reaction medium [ 62 – 64 ].…”

Section: Introductionmentioning

confidence: 99%

Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

Yıldırım

2024

Beilstein J. Org. Chem.

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Tandem Diels–Alder reactions are often used for the straightforward formation of complex natural compounds and the fused polycyclic systems contained in their precursors. In the second step of this reaction, regio- and stereochemically controlled intramolecular cyclization leads to the formation of versatile nitrogen-containing tricyclic systems. However, these useful organic transformations are usually carried out in highly toxic organic solvents such as benzene, toluene, chloroform, etc. Despite recent efforts by 'green chemists', synthetic chemists still use these traditional toxic organic solvents in many of their reactions, even though safer alternatives are available. However, in addition to the harmful effects of these petrochemical solvents on the environment, the prediction that their resources will run out in the near future has led 'green chemists' to explore solvents that can be derived from renewable resources and used effectively in various organic transformations. In this context, we have shown for the first time that the 100% atom-economical tandem Diels–Alder reaction between aminofuranes and maleic anhydride can be carried out successfully in vegetable oils and waxes. The reaction was successfully carried out in sunflower seed oil, olive oil, oleic acid and lauryl myristate under mild reaction conditions. A series of epoxyisoindole-7-carboxylic acid and bisepoxyisoindole-7-carboxylic acids were obtained in good yields after a practical isolation procedure. The results obtained in this study demonstrate the potential of vegetable oils and their renewable materials to provide a reaction medium that is more sustainable than conventional organic solvents in cascade Diels–Alder reactions and can be used repeatedly without significant degradation. These materials also allow the reaction to be completed in less time, with less energy consumption and higher yields.

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“…Yan zincir kısmında (tether de) N-KG ve O içeren furan çekirdekli bileşiklerin organik kimyada oldukça zor olan trisiklik ve tetrasiklik fused halkalaşma ürünleri tek adımda Termal ve mikrodalga yöntemle intramoleküler [4+2] Diels-Alder reaksiyonları sonucu elde edilebilmektedir [3,4].…”

Section: Introductionunclassified

Furan Çekirdekli Bileşiklerin Mikrodalga Destekli Molekül İçi Diels Alder Halkalaşma Reaksiyonları

Karaarslan¹

2018

deufmd

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Bu çalışmada furan çekirdekli bileşiklerin İntra Moleküler (Molekül İçi) Diels-Alder (İMDA) halkalaşma reaksiyonu mikrodalga yöntemlere gerçekleştirilmiş ve bitişik üç halkalı bileşikler elde edilmiştir. Reaksiyonlar çözücüsüz ortamda ve herhangi bir metal katalizörü kullanmadan gerçekleştirilmiştir. Oksijen yan zincirli başlangıç maddeleri furan çekirdekli bileşiklerin direk alkilasyonu ile elde edilirken, azot yan zincirli başlangıç maddeleri alkilasyondan sonra koruma işlemi yapılarak elde edilmiştir. Halkalaşma reaksiyonları için ticari mikrodalga fırın (2450 MHz) kullanılmıştır. Yapılan deneylerin verimleri daha önceden yapılmış olan klasik termal halkalaşma reaksiyonları ile karşılaştırılmıştır. Mikrodalga destekli reaksiyonlardan elde edilen verimlerin termal reaksiyonlardan elde edilen sonuçlarla karşılaştırılabilir nitelikte oldukları sonucuna ulaşılmıştır.

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Microwave assisted IMDAF# reaction: Microwave irradiation applied with success to cycloaddition reaction of N-propargyl-N-p-tolyl-N-2-furfurylamines

Cited by 10 publications

References 11 publications

Synthesis of Phenanthridine Derivatives by Microwave-Mediated Cyclization of o-Furyl(allylamino)arenes

Synthesis of Phenanthridine Derivatives by Microwave-Mediated Cyclization of o-Furyl(allylamino)arenes

Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

Furan Çekirdekli Bileşiklerin Mikrodalga Destekli Molekül İçi Diels Alder Halkalaşma Reaksiyonları

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