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'''1,1-Dimethylurea''' ('''DMU''') is a ] derivative used as a ] and a ] in ] reactions. It is a solid, but forms a ] with a low ] in combination with various ] additives that can serve as a ] solvent for various chemical reactions.<ref>{{cite journal |doi= 10.1016/j.tet.2014.11.024 |title= Diversity-oriented approach to spirocycles with indole moiety via Fischer indole cyclization, olefin metathesis and Suzuki–Miyaura cross-coupling reactions |date= 2015 |last1= Kotha |first1= Sambasivarao |last2= Ali |first2= Rashid |last3= Srinivas |first3= Venu |last4= Krishna |first4= Nimita G. |journal= Tetrahedron |volume= 71 |pages= 129–138 }}</ref><ref>{{cite journal |doi= 10.1002/cctc.201402415 |title= Superparamagnetic CuFeO<sub>2</sub> Nanoparticles in Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Imidazo&#91;1,2- ''a'' &#93;pyridines |date= 2014 |last1= Lu |first1= Jun |last2= Li |first2= Xiao-Tang |last3= Ma |first3= Er-Qian |last4= Mo |first4= Li-Ping |last5= Zhang |first5= Zhan-Hui |journal= ChemCatChem |volume= 6 |issue= 10 |pages= 2854–2859 }}</ref><ref>{{cite journal |doi= 10.1039/b414515a |title= Low-melting sugar–urea–salt mixtures as solvents for Diels–Alder reactions |date= 2005 |last1= Imperato |first1= Giovanni |last2= Eibler |first2= Ernst |last3= Niedermaier |first3= Julia |last4= König |first4= Burkhard |journal= Chem. Commun. |issue= 9 |pages= 1170–1172 |pmid= 15726181 }}</ref><ref>{{cite journal |doi= 10.1039/B816551C |title= Organic reactions in low melting mixtures based on carbohydrates and l-carnitine—a comparison |date= 2009 |last1= Ilgen |first1= Florian |last2= König |first2= Burkhard |journal= Green Chemistry |volume= 11 |issue= 6 |page= 848 }}</ref> The un] nitrogen can serve as a ] for a wide range of reactions, including reaction with ]s to form ]s,<ref>{{cite journal |doi= 10.1021/jm0498351 |title= Tetramethylcyclopropyl Analogue of a Leading Antiepileptic Drug, Valproic Acid. Synthesis and Evaluation of Anticonvulsant Activity of Its Amide Derivatives |date= 2004 |last1= Sobol |first1= Eyal |last2= Bialer |first2= Meir |last3= Yagen |first3= Boris |journal= Journal of Medicinal Chemistry |volume= 47 |issue= 17 |pages= 4316–4326 |pmid= 15294003 }}</ref> ] with ]s,<ref>{{cite journal |doi= 10.1002/ejoc.201403405 |title= Efficient and Selective Palladium-Catalysed C-3 Urea Couplings to 3,5-Dichloro-2(1 ''H'' )-pyrazinones |date= 2015 |last1= Belfrage |first1= Anna Karin |last2= Gising |first2= Johan |last3= Svensson |first3= Fredrik |last4= Åkerblom |first4= Eva |last5= Sköld |first5= Christian |last6= Sandström |first6= Anja |journal= European Journal of Organic Chemistry |issue= 5 |pages= 978–986 }}</ref> and ] ] with ]s.<ref>{{cite journal |doi= 10.13040/IJPSR.0975-8232.9(8).3322-27 |date= 2018 |journal= International Journal of Pharmaceutical Sciences and Research |volume= 9 |issue= 8 }}</ref> The unsubstituted ]-like portion can undergo ] coupling with ]s to give dihydro]s.<ref>{{cite journal |doi= 10.1002/anie.201904662 |title= Regioselective Formal &#91;3+2&#93; Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation |date= 2019 |last1= Wu |first1= Fan |last2= Alom |first2= Nur-E |last3= Ariyarathna |first3= Jeewani P. |last4= Naß |first4= Johannes |last5= Li |first5= Wei |journal= Angewandte Chemie International Edition |volume= 58 |issue= 34 |pages= 11676–11680 |pmid= 31211504 }}</ref> '''1,1-Dimethylurea''' ('''DMU''') is a ] derivative used as a ] and a ] in ] reactions. It is a solid, but forms a ] with a low ] in combination with various ] additives that can serve as a ] solvent for various chemical reactions.<ref>{{cite journal |doi= 10.1016/j.tet.2014.11.024 |title= Diversity-oriented approach to spirocycles with indole moiety via Fischer indole cyclization, olefin metathesis and Suzuki–Miyaura cross-coupling reactions |date= 2015 |last1= Kotha |first1= Sambasivarao |last2= Ali |first2= Rashid |last3= Srinivas |first3= Venu |last4= Krishna |first4= Nimita G. |journal= Tetrahedron |volume= 71 |pages= 129–138 }}</ref><ref>{{cite journal |doi= 10.1002/cctc.201402415 |title= Superparamagnetic CuFeO<sub>2</sub> Nanoparticles in Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Imidazopyridines |date= 2014 |last1= Lu |first1= Jun |last2= Li |first2= Xiao-Tang |last3= Ma |first3= Er-Qian |last4= Mo |first4= Li-Ping |last5= Zhang |first5= Zhan-Hui |journal= ChemCatChem |volume= 6 |issue= 10 |pages= 2854–2859 }}</ref><ref>{{cite journal |doi= 10.1039/b414515a |title= Low-melting sugar–urea–salt mixtures as solvents for Diels–Alder reactions |date= 2005 |last1= Imperato |first1= Giovanni |last2= Eibler |first2= Ernst |last3= Niedermaier |first3= Julia |last4= König |first4= Burkhard |journal= Chem. Commun. |issue= 9 |pages= 1170–1172 |pmid= 15726181 }}</ref><ref>{{cite journal |doi= 10.1039/B816551C |title= Organic reactions in low melting mixtures based on carbohydrates and <small>L</small>-carnitine—a comparison |date= 2009 |last1= Ilgen |first1= Florian |last2= König |first2= Burkhard |journal= Green Chemistry |volume= 11 |issue= 6 |page= 848 }}</ref> The un] nitrogen, as an ]-like region, can serve as a ] for a wide range of reactions, including reaction with ]s to form ]s,<ref>{{cite journal |doi= 10.1021/jm0498351 |title= Tetramethylcyclopropyl Analogue of a Leading Antiepileptic Drug, Valproic Acid. Synthesis and Evaluation of Anticonvulsant Activity of Its Amide Derivatives |date= 2004 |last1= Sobol |first1= Eyal |last2= Bialer |first2= Meir |last3= Yagen |first3= Boris |journal= Journal of Medicinal Chemistry |volume= 47 |issue= 17 |pages= 4316–4326 |pmid= 15294003 }}</ref> ] with ]s,<ref>{{cite journal |doi= 10.1002/ejoc.201403405 |title= Efficient and Selective Palladium-Catalysed C-3 Urea Couplings to 3,5-Dichloro-2(1''H'')-pyrazinones |date= 2015 |last1= Belfrage |first1= Anna Karin |last2= Gising |first2= Johan |last3= Svensson |first3= Fredrik |last4= Åkerblom |first4= Eva |last5= Sköld |first5= Christian |last6= Sandström |first6= Anja |journal= European Journal of Organic Chemistry |issue= 5 |pages= 978–986 }}</ref> and ] ] with ]s.<ref>{{cite journal |doi= 10.13040/IJPSR.0975-8232.9(8).3322-27 |date= 2018 |journal= International Journal of Pharmaceutical Sciences and Research |volume= 9 |issue= 8 |pages= 3322–3327 |first1= Anis |last1= Ahamed |first2= Ibrahim A. |last2= Arif |first3= Meera |last3= Moydeen |first4= Radhakrishnan Surendra |last4= Kumar |first5= Akbar |last5= Idhayadhulla |title= In-Vitro Antibacterial and Cytotoxicity Evaluation of Some Novel Tetrazole Derivatives }}</ref> The unsubstituted ]-like portion can undergo ] coupling with ]s to give dihydro]s.<ref>{{cite journal |doi= 10.1002/anie.201904662 |title= Regioselective Formal Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation |date= 2019 |last1= Wu |first1= Fan |last2= Alom |first2= Nur-E |last3= Ariyarathna |first3= Jeewani P. |last4= Naß |first4= Johannes |last5= Li |first5= Wei |journal= Angewandte Chemie International Edition |volume= 58 |issue= 34 |pages= 11676–11680 |pmid= 31211504 }}</ref>


== References == == References ==

Revision as of 10:55, 18 December 2024

1,1-Dimethylurea
Names
IUPAC name 1,1-Dimethylurea
Other names N,N-Dimethylurea
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

1,1-Dimethylurea (DMU) is a urea derivative used as a polar solvent and a reagent in organic reactions. It is a solid, but forms a eutectic with a low melting point in combination with various hydroxylic additives that can serve as a environmentally sustainable solvent for various chemical reactions. The unsubstituted nitrogen, as an amine-like region, can serve as a nucleophile for a wide range of reactions, including reaction with acyl halides to form acylureas, coupling with vinyl halides, and multi-component condensation reaction with aldehydes. The unsubstituted amide-like portion can undergo oxidative coupling with alkenes to give dihydrooxazoles.

References

  1. Kotha, Sambasivarao; Ali, Rashid; Srinivas, Venu; Krishna, Nimita G. (2015). "Diversity-oriented approach to spirocycles with indole moiety via Fischer indole cyclization, olefin metathesis and Suzuki–Miyaura cross-coupling reactions". Tetrahedron. 71: 129–138. doi:10.1016/j.tet.2014.11.024.
  2. Lu, Jun; Li, Xiao-Tang; Ma, Er-Qian; Mo, Li-Ping; Zhang, Zhan-Hui (2014). "Superparamagnetic CuFeO2 Nanoparticles in Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Imidazopyridines". ChemCatChem. 6 (10): 2854–2859. doi:10.1002/cctc.201402415.
  3. Imperato, Giovanni; Eibler, Ernst; Niedermaier, Julia; König, Burkhard (2005). "Low-melting sugar–urea–salt mixtures as solvents for Diels–Alder reactions". Chem. Commun. (9): 1170–1172. doi:10.1039/b414515a. PMID 15726181.
  4. Ilgen, Florian; König, Burkhard (2009). "Organic reactions in low melting mixtures based on carbohydrates and L-carnitine—a comparison". Green Chemistry. 11 (6): 848. doi:10.1039/B816551C.
  5. Sobol, Eyal; Bialer, Meir; Yagen, Boris (2004). "Tetramethylcyclopropyl Analogue of a Leading Antiepileptic Drug, Valproic Acid. Synthesis and Evaluation of Anticonvulsant Activity of Its Amide Derivatives". Journal of Medicinal Chemistry. 47 (17): 4316–4326. doi:10.1021/jm0498351. PMID 15294003.
  6. Belfrage, Anna Karin; Gising, Johan; Svensson, Fredrik; Åkerblom, Eva; Sköld, Christian; Sandström, Anja (2015). "Efficient and Selective Palladium-Catalysed C-3 Urea Couplings to 3,5-Dichloro-2(1H)-pyrazinones". European Journal of Organic Chemistry (5): 978–986. doi:10.1002/ejoc.201403405.
  7. Ahamed, Anis; Arif, Ibrahim A.; Moydeen, Meera; Kumar, Radhakrishnan Surendra; Idhayadhulla, Akbar (2018). "In-Vitro Antibacterial and Cytotoxicity Evaluation of Some Novel Tetrazole Derivatives". International Journal of Pharmaceutical Sciences and Research. 9 (8): 3322–3327. doi:10.13040/IJPSR.0975-8232.9(8).3322-27.
  8. Wu, Fan; Alom, Nur-E; Ariyarathna, Jeewani P.; Naß, Johannes; Li, Wei (2019). "Regioselective Formal Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation". Angewandte Chemie International Edition. 58 (34): 11676–11680. doi:10.1002/anie.201904662. PMID 31211504.
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