Parallel Synthesis of Arrays of Amino-Acid-Derived Isocyanoamides Useful As Starting Materials in IMCR

Abstract

Arrays of amino-acid-derived isocyanoamides are conveniently produced on a multigram scale in one step by the solventless aminolysis of the corresponding methyl esters with primary or secondary aliphatic amines. Most of the corresponding isocyanides precipitate during the reaction and can be filtered to yield highly pure, colorless, and odorless solids. They are potentially useful in the combinatorial chemistry of multicomponent reactions.

Isoselenocyanates derived from amino acid esters: an expedient synthesis and application to the assembly of selenoureidopeptidomimetics, unsymmetrical Selenoureas and selenohydantoins

“…The protocol was then extended to prepare few isoselenocyanato carboxamides also. Unlike esters and α‐isocyano carboxamides are stable solids and odorless but retain the isocyanide reactivity in isocyanide based multicomponent reactions (IMCRs)47, 48. Four complementary protocols are available to access this important starting material48, 49.…”

“…Unlike esters and α‐isocyano carboxamides are stable solids and odorless but retain the isocyanide reactivity in isocyanide based multicomponent reactions (IMCRs)47, 48. Four complementary protocols are available to access this important starting material48, 49. To implement our other objective in making α‐isoselenocyanato carboxamides 5 (Figure 3), six known α‐isocyano carboxamides were made employing known procedure.…”

Brønsted Acid Catalyzed Enantioselective Three‐Component Reaction Involving the α Addition of Isocyanides to Imines

“…[10] We have recently reported that the chiral aluminum-salen (salen = N,N-bis(salicylidene)ethylenediamine) complex [11] was an efficient catalyst for the enantioselective Passerini three-component reaction. [14,15] As a prelude of our work, we examined the reaction of the preformed imine 6 a (R 1 = tBu) and the a-isocyanoacetamide 4 a (R 2 = Bn) [16] in the presence of chiral phosphoric acids. To the best of our knowledge, there is no single report on Ugi-type reactions which involve the a addition of isocyanides to imines for generating the chiral centers.…”

Silver‐Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone‐Fused Carbo‐ and Heterocycles

“…(1)]. [1,16] Therefore,b roader exploration of the reactivity profiles of both aryl isocyanides and isocyanoacetamides remains highly desirable. [10][11][12] Meanwhile, isocyanoacetamides are mainly known for the carbene-like reactivity of the isocyano group when used as af ive-atom component in multicomponent reactions [1,13] or palladiumcatalyzed imidoylative cyclization reactions, [14] and the acarbon atom of isocyanoacetamides has only been shown to serve as anucleophile in formal [3+ +2] cycloaddition [1,10,15] and alkylation reactions.…”