Regiochemistry of N??substitution of some 4 (5)??substituted imidazoles under solvent??free conditions

…, M Haukka, P Vainiotalo, P Aulaskari

Index: Oresmaa, Larisa; Taberman, Helena; Haukka, Matti; Vainiotalo, Pirjo; Aulaskari, Paula Journal of Heterocyclic Chemistry, 2007 , vol. 44, # 6 p. 1445 - 1451

Full Text: HTML

Citation Number: 6

Abstract

Imidazole nitrogen can be substituted by applying an alkyl halide as electrophile under basic conditions. Alkylations have also been carried out in neutral conditions, but since the imidazolate anion is a far more effective nucleophile, most alkylations are done in basic conditions. For 2-substituted and symmetrically substituted compounds the reaction is straightforward, although quaternization may occasionally be a problem. Typically N- ...

Related Articles:

Supported TBD-assisted solution phase diversification of formyl-aza-heterocycles through alkylation-knoevenagel one pot sequences

[Maatougui, Abdelaziz El; Crespo, Abel; Silva, Artur M.S.; Coelho, Alberto Combinatorial Chemistry and High Throughput Screening, 2011 , vol. 14, # 7 p. 570 - 582]

Regioselective Alkylation of 2-Alkyl-5, 6, 7, 8-tetrahydro-3H-cycloheptimidazol-4-ones and 2-Alkyl-3H-cycloheptimidazol-4-ones

[Sonegawa, Motoharu; Yokota, Masayuki; Tomiyama, Hiroshi; Tomiyama, Tsuyoshi Chemical and Pharmaceutical Bulletin, 2006 , vol. 54, # 5 p. 706 - 710]

Regioselective Alkylation of 2-Alkyl-5, 6, 7, 8-tetrahydro-3H-cycloheptimidazol-4-ones and 2-Alkyl-3H-cycloheptimidazol-4-ones

[Sonegawa, Motoharu; Yokota, Masayuki; Tomiyama, Hiroshi; Tomiyama, Tsuyoshi Chemical and Pharmaceutical Bulletin, 2006 , vol. 54, # 5 p. 706 - 710]

Synthesis of N1-Aryl-and N1-Benzyl Substituted Imidazole-4-and Imidazole-5-carbaldehydes

[Antonini, Ippolito; Cristalli, Gloria; Franchetti, Palmarisa; Grifantini, Mario; Martelli, Sante Synthesis, 1983 , # 1 p. 47 - 49]

More Articles...