A simple synthesis of dimethyl 2-[(Z)-3-amino-1-oxo-1-(substituted)but-2-en-2-yl]fumarates: potential intermediates in the synthesis of polysubstituted five- and six-membered heterocycles

2016 ◽  
Vol 71 (6) ◽  
pp. 677-682 ◽  
Author(s):  
Rok Šinkovec ◽  
Uroš Grošelj ◽  
Benjamin Prek ◽  
Marta Počkaj ◽  
Sebastijan Ričko ◽  
...  
Keyword(s):  
Ammonium Acetate ◽  
Dimethyl Acetal ◽  
Simple Synthesis ◽  
Dimethyl Acetylenedicarboxylate ◽  
Methyl Ketones ◽  
Metal Free

AbstractIn this communication, a simple synthesis of dimethyl 2-[(Z)-3-amino-1-oxo-1-(substituted)but-2-en-2-yl]fumarates is described. Methyl ketones were transformed by treatment with N,N-dimethylacetamide dimethyl acetal (DMADMA) into 3-dimethylamino-1-(substituted)but-2-en-1-ones, followed by treatment with ammonium acetate into (Z)-3-amino-1-(substituted)but-2-en-1-ones and addition to dimethyl acetylenedicarboxylate. These novel polysubstituted butadienes are potential intermediates for the metal-free preparation of polysubstituted five- and six-membered heterocycles.

Reactions of Methyl Ketones and (Hetero)arylcarboxamides with N,N-Dimethylacetamide Dimethyl Acetal. A Simple Metal-Free Synthesis of 2,4,6-Trisubstituted Pyridines

2015 ◽  
Vol 68 (2) ◽  
pp. 184 ◽  
Author(s):  
Benjamin Prek ◽  
Uroš Grošelj ◽  
Marta Kasunič ◽  
Silvo Zupančič ◽  
Jurij Svete ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Single Crystal ◽  
Ammonium Acetate ◽  
Dimethyl Acetal ◽  
Methyl Ketones ◽  
Closed Vessel ◽  
Simple Metal ◽  
One Pot ◽  
X Ray ◽  
Metal Free

Two metal-free syntheses of 2,4,6-trisubstituted pyridines 10a–m and 16a–j are described. N,N,6-Trimethyl-4-(substituted)pyridin-2-amines 10 were prepared from aryl or heteroaryl methyl ketones which were transformed with N,N-dimethylacetamide dimethyl acetal (DMADMA) into enaminones 4a–m, followed by treatment with ammonium acetate to give (Z)-3-amino-1-(substituted)but-2-en-1-ones 5a–m. These were treated with DMADMA under microwave irradiation in a closed vessel at 130°C, to give via intermediates 7–9 the final products 10a–m. N2,N2,N4,N4-Tetramethyl-6-(substituted) pyridine-2,4-diamines 16a–j were prepared in a one-pot synthesis from the corresponding carboxamides 11a–j by treatment with an excess of DMADMA in a closed vessel under microwave irradiation to give via intermediates 12a–j to 15a–j the final products 16a–j. X-Ray single crystal diffractometry studies of the enaminones 5c, 5g, 5i, 5j, and 5m and 2,4,6-trisubstituted pyridines 16a, 16b, 16g, 16i, and 16j were consistent with the expected structures.

A Simple Metal-free Synthesis of 2,4,5-Trisubstituted Pyridines and Pyridine N-Oxides by [2+2] Cycloaddition of Enaminones to Propyne Iminium Salts

2014 ◽  
Vol 69 (5) ◽  
pp. 554-566 ◽  
Author(s):  
Jure Bezenšek ◽  
Benjamin Prek ◽  
Uroš Grošelj ◽  
Amalija Golobič ◽  
Katarina Stare ◽  
...  
Keyword(s):  
Dimethyl Acetal ◽  
Methyl Ketones ◽  
Simple Metal ◽  
One Pot ◽  
Alkyl Aryl ◽  
Metal Free ◽  
Iminium Salts

Herein a simple one-pot metal-free synthesis of 2,4,5-trisubstituted pyridines and pyridine Noxides by [2+2] cycloaddition of enaminones, which are prepared in situ from alkyl, aryl and heteroaryl methyl ketones using N,N-dimethylformamide dimethyl acetal (DMFDMA), and propyne iminium salts as electron-poor acetylenes, is described.

Metal-Free Oxidative Thioesterification of Methyl Ketones with Thiols/Disulfides for the Synthesis of α-Ketothioesters

2018 ◽  
Vol 83 (24) ◽  
pp. 14978-14986 ◽  
Author(s):  
Biao Hu ◽  
Pan Zhou ◽  
Qiaohe Zhang ◽  
Yanqin Wang ◽  
Siyun Zhao ◽  
...  
Keyword(s):  
Methyl Ketones ◽  
Metal Free

Transition metal-free C(sp3)–H bond coupling among three methyl groups

2017 ◽  
Vol 53 (38) ◽  
pp. 5346-5349 ◽  
Author(s):  
Yufeng Liu ◽  
Xi Zhan ◽  
Pengyi Ji ◽  
Jingwen Xu ◽  
Qiang Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Methyl Groups ◽  
Methyl Ketones ◽  
Reaction Conditions ◽  
Methyl Group ◽  
Metal Free

A coupling of multiple C(sp3)–H bonds of the methyl group in methyl ketones with dimethyl sulfoxides was developed under transition metal-free reaction conditions.

Microwave-Assisted, One-Pot Reaction of Pyridines, α-Bromoketones and Ammonium Acetate: An Efficient and Simple Synthesis of Imidazo[1,2-a]-pyridines

Synlett ◽  
2010 ◽  
Vol 2010 (11) ◽  
pp. 1606-1608 ◽  
Author(s):  
Mehdi Adib ◽  
Hamid Bijanzadeh ◽  
Ali Mohamadi ◽  
Ehsan Sheikhi ◽  
Samira Ansari
Keyword(s):  
Ammonium Acetate ◽  
Simple Synthesis ◽  
One Pot ◽  
Microwave Assisted

Convenient Synthesis of Furo[3,2-b]quinolin-4(1H)-ones

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 911-915
Author(s):  
Veronika Králová ◽  
Miroslav Soural ◽  
Radim Horák ◽  
Pavel Hradil
Keyword(s):  
Methanesulfonic Acid ◽  
Starting Material ◽  
Simple Synthesis ◽  
Reaction Intermediates ◽  
Metal Free ◽  
Convenient Synthesis

In this work, we report the simple synthesis of furo[3,2-b]quinolin-4(1H)-ones from readily available 4-ethynyl-[1,3]dioxolo[4,5-c]quinolone as the key starting material. After Sonogashira (hetero)arylation, formation of the furoquinoline scaffold was accomplished using methanesulfonic acid and metal-free conditions. Although the cyclization was affected by the substitution of reaction intermediates, the method allowed the preparation of derivatives varying at the C3-position.

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