Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds

• Yuki Nakanishi,
• Shoichi Sugita,
• Kentaro Okano and
• Atsunori Mori

Beilstein J. Org. Chem. 2024, 20, 3256–3262, doi:10.3762/bjoc.20.269

• previous result for the cyclization of 5b to afford the doubly cyclized product 6b (reported yield: 85% [23]), suggesting that the superior reactivity was found for bifunctional bisamides compared to monoamides. It was also found that the reaction also is applicable to a carbocyclic amide derivative. When

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

• Alexander V. Tsygankov,
• Vladyslav O. Vereshchak,
• Tetiana O. Savluk,
• Serhiy M. Desenko,
• Valeriia V. Ananieva,
• Oleksandr V. Buravov,
• Yana I. Sakhno,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

• University, Svobody sq., 4, 61022, Kharkiv, Ukraine 10.3762/bjoc.20.156 Abstract By one-pot four- and three-component Ugi reactions involving convertible isocyanides and unexplored pyrrole-containing β-chlorovinylaldehyde, a small library of 20 bisamides with unusual behavior in post-Ugi transformations was

• prepared and characterized. Surprisingly, a well-documented approach to obtain peptide-containing carboxylic acids through acid hydrolysis of the convertible isocyanide moiety in the Ugi bisamides proceeded in an unexpected manner in our case, leading to the formation of derivatives of amides of

• -called convertible isocyanides [27][28][29][30][31][32][33][34][35][36] in Ugi-4CR makes it possible to obtain carboxylic acids or esters after hydrolysis of the secondary amide group in the Ugi products (Scheme 2) [27][28][29][31][32][34][35][36]. Ugi bisamides modified in this way may be subsequently

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