Anodic oxidation of bisamides from diaminoalkanes by constant current electrolysis

• Tatiana Golub and
• James Y. Becker

Beilstein J. Org. Chem. 2018, 14, 861–868, doi:10.3762/bjoc.14.72

• Tatiana Golub James Y. Becker Department of Chemistry, Ben-Gurion University of the Negev, Beer Sheva 84105, Israel 10.3762/bjoc.14.72 Abstract In general, bisamides derived from diamines and involving 3 and 4 methylene groups as spacers between the two amide functionalities behave similar to

• : anodic oxidation; bisamides; constant current electrolysis; methoxylation; Introduction It is well known that the anodic oxidation of amides involving a hydrogen atom at the α-position to the N atom could undergo alkoxylation, carboxylation and hydroxylation at this position [1][2][3][4][5] (Scheme 1

• pharmaceutical compounds. For instance, symmetrical and unsymmetrical bisamides derived from diamines are significant components as structural subunits for the construction of peptidomimetric frameworks [18] and as lubricants [19]. To the best of our knowledge nothing has been known so far about electrochemical

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

• Gijs Koopmanschap,
• Eelco Ruijter and
• Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

• orthogonally protected carbohydrate-derived azido-acetal and trimethylphosphine yielded the necessary cyclic imine, which then was exposed to benzoic acid and different isocyanides. The resulting Ugi-bisamides 163 were obtained in moderate to good yields (22–78%), in which the more sterically demanding

Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

• Andivelu Ilangovan and
• Shanmugasundar Saravanakumar

Beilstein J. Org. Chem. 2014, 10, 127–133, doi:10.3762/bjoc.10.9

• Andivelu Ilangovan Shanmugasundar Saravanakumar School of Chemistry, Bharathidasan University, Tiruchirappalli, 620024, India Syngene International Ltd., Bangalore, 560 099, India 10.3762/bjoc.10.9 Abstract A unified strategy was followed for the synthesis of three putrescine bisamides

• ; dasyclamide; gigantamide A; (+)-grandiamide D; natural products; putrescine bisamides; Introduction Putrescine bisamides are one of the important naturally occurring polyamine alkaloids found in open chain and cyclic forms. The genera Aglaia are the richest source of putrescine bisamides. The cyclic 2

• -aminopyrrolidine compounds are synthesised in plants from open-chained bisamides by enzymatic cyclization. It is assumed that both forms of bisamides undergo a cycloaddition reaction with a co-occurring flavanol to form highly bioactive flavaglines [1][2]. For example, odorine (2) acted as a building block for

Synthesis of methylenebisamides using CC- or DCMT- activated DMSO

• Qiang Wang,
• Lili Sun,
• Yu Jiang and
• Chunbao Li

Beilstein J. Org. Chem. 2008, 4, No. 51, doi:10.3762/bjoc.4.51

• 315211, China. 10.3762/bjoc.4.51 Abstract Bisamides are key fragments for the introduction of gem-diaminoalkyl residues into retroinverso pseudopeptide derivatives and in the synthesis of peptidomimetic compounds. The literature methods for these types of compounds have certain drawbacks. In particular

• reaction of nucleophilic reagents such as amides, alcohols, and phenols with DMSO activated by CC. The amide moiety is an important constituent of many biologically significant compounds. Bisamides are of considerable interest in the synthesis of peptidomimetic compounds [15]. In particular, bisamides are