Literature DB >> 26576065

Copper-mediated N-Arylation of Methyl 2-Aminothiophene-3-carboxylate with Organoboron Reagents.

Komal Rizwan1, Idris Karakaya2, Drew Heitz3, Muhammad Zubair4, Nasir Rasool4, Gary A Molander3.   

Abstract

A practical protocol for the synthesis of N-arylated methyl 2-aminothiophene-3-carboxylate has been developed via Chan-Lam cross-coupling. The desired products were synthesized by cross-coupling of methyl 2-aminothiophene-3-carboxylate with both arylboronic acids and potassium aryltrifluoroborate salts in moderate to good yields. A broad range of functional groups was well tolerated.

Entities:  

Keywords:  amine; aryltrifluoroborate; carboxylate; copper; cross-coupling; thiophene

Year:  2015        PMID： 26576065      PMCID： PMC4643285          DOI： 10.1016/j.tetlet.2015.10.080

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  22 in total

1.  Fused thiophene derivatives as MEK inhibitors.

Authors:  Victoria E Laing; Daniel C Brookings; Rachel J Carbery; Jose Gascon Simorte; Martin C Hutchings; Barry J Langham; Martin A Lowe; Rodger A Allen; Joanne R Fetterman; James Turner; Christoph Meier; Jeff Kennedy; Mark Merriman
Journal:  Bioorg Med Chem Lett       Date:  2011-11-06       Impact factor: 2.823

Review 2.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

3.  All-polymer field-effect transistor realized by printing techniques.

Authors:  F Garnier; R Hajlaoui; A Yassar; P Srivastava
Journal:  Science       Date:  1994-09-16       Impact factor: 47.728

4.  Synthesis of an acyltrifluoroborate and its fusion with azides to form amides.

Authors:  Gary A Molander; Jessica Raushel; Noel M Ellis
Journal:  J Org Chem       Date:  2010-06-18       Impact factor: 4.354

5.  Optimization of Potent Inhibitors of P. falciparum Dihydroorotate Dehydrogenase for the Treatment of Malaria.

Authors:  Renato T Skerlj; Cecilia M Bastos; Michael L Booker; Martin L Kramer; Robert H Barker; Cassandra A Celatka; Thomas J O'Shea; Benito Munoz; Amar Bir Sidhu; Joseph F Cortese; Sergio Wittlin; Petros Papastogiannidis; Inigo Angulo-Barturen; Maria Belen Jimenez-Diaz; Edmund Sybertz
Journal:  ACS Med Chem Lett       Date:  2011-07-11       Impact factor: 4.345

6.  Copper(II) complexes with substituted thiosemicarbazones of thiophene-2-carboxaldehyde: synthesis, characterization and antiamoebic activity against E. histolytica.

Authors:  Sangita Sharma; Fareeda Athar; Mannar R Maurya; Amir Azam
Journal:  Eur J Med Chem       Date:  2005-08-29       Impact factor: 6.514

7.  Synthesis and antiallergy activity of 10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidines and 10-oxo-10H-pyrido[1,2-a]thieno[3,4-d]pyrimidines.

Authors:  D T Connor; R J Sorenson; W A Cetenko; J J Kerbleski; F J Tinney
Journal:  J Med Chem       Date:  1984-04       Impact factor: 7.446

8.  Screening for antidepressant, sedative and analgesic activities of novel fused thiophene derivatives.

Authors:  Wagnat W Wardakhan; Omar M E Abdel-Salam; Gamal A Elmegeed
Journal:  Acta Pharm       Date:  2008-03       Impact factor: 2.230

9.  [11C]olanzapine, radiosynthesis and lipophilicity of a new potential PET 5-HT2 and D2 receptor radioligand.

Authors:  Mingzhang Gao; Zenas Shi; Min Wang; Qi-Huang Zheng
Journal:  Bioorg Med Chem Lett       Date:  2013-02-14       Impact factor: 2.823

10.  The identification of 2-(1H-indazol-4-yl)-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (GDC-0941) as a potent, selective, orally bioavailable inhibitor of class I PI3 kinase for the treatment of cancer .

Authors:  Adrian J Folkes; Khatereh Ahmadi; Wendy K Alderton; Sonia Alix; Stewart J Baker; Gary Box; Irina S Chuckowree; Paul A Clarke; Paul Depledge; Suzanne A Eccles; Lori S Friedman; Angela Hayes; Timothy C Hancox; Arumugam Kugendradas; Letitia Lensun; Pauline Moore; Alan G Olivero; Jodie Pang; Sonal Patel; Giles H Pergl-Wilson; Florence I Raynaud; Anthony Robson; Nahid Saghir; Laurent Salphati; Sukhjit Sohal; Mark H Ultsch; Melanie Valenti; Heidi J A Wallweber; Nan Chi Wan; Christian Wiesmann; Paul Workman; Alexander Zhyvoloup; Marketa J Zvelebil; Stephen J Shuttleworth
Journal:  J Med Chem       Date:  2008-09-25       Impact factor: 7.446
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