2619-16-1Relevant academic research and scientific papers
KOtBu-Catalyzed Michael Addition Reactions Under Mild and Solvent-Free Conditions
Thiyagarajan, Subramanian,Krishnakumar, Varadhan,Gunanathan, Chidambaram
supporting information, p. 518 - 523 (2020/02/04)
Designed transition metal complexes predominantly catalyze Michael addition reactions. Inorganic and organic base-catalyzed Michael addition reactions have been reported. However, known base-catalyzed reactions suffer from the requirement of solvents, additives, high pressure and also side-reactions. Herein, we demonstrate a mild and environmentally friendly strategy of readily available KOtBu-catalyzed Michael addition reactions. This simple inorganic base efficiently catalyzes the Michael addition of underexplored acrylonitriles, esters and amides with (oxa-, aza-, and thia-) heteroatom nucleophiles. This catalytic process proceeds under solvent-free conditions and at room temperature. Notably, this protocol offers an easy operational procedure, broad substrate scope with excellent selectivity, reaction scalability and excellent TON (>9900). Preliminary mechanistic studies revealed that the reaction follows an ionic mechanism. Formal synthesis of promazine is demonstrated using this catalytic protocol.
Tributylphosphine, excellent organocatalyst for conjugate additions of non-nucleophilic N-containing compounds
Gimbert, Carolina,Moreno-Ma?as, Marcial,Pérez, Elisabet,Vallribera, Adelina
, p. 8305 - 8310 (2008/02/05)
Conjugate additions of non-nucleophilic N-containing compounds such as amides, thioamides, sulfonamides, and electron-poor anilines with different Michael acceptors can be promoted through the use of tributylphosphine. The range of useful pKa's of nucleophiles has been established (pKa25) and new insights into the mechanism proposed.
MACROCYCLIC AND MACROPOLYCYCLIC COMPOUNDS BASED UPON 1,3-DISUBSTITUTED PROPANE UNITS
Pratt, John A. E.,Sutherland, Ian O.,Newton, Roger F.
, p. 13 - 22 (2007/10/02)
Synthetic routes to the macrocyclic polyamine derivatives (1) and (3) are described, together with an investigation of the complexing properties of the triamines (1d) and (3d) with primary alkylammonium cations.Macrotricyclic and macrotetracyclic compounds may be obtained from the macrocycle (1) by a stepwise procedure whereas macrocycle (3b) can be converted into a macrotricyclic derivative in a one step alkylation procedure.The alkylation of the tetrahydropyrimidone (18) with α,α'-dibromo-m-xylene gives the calix arene analogue (19) which adopts the 'cone' (21a) and '1,3-alternate' (21b) conformations.The macrocyclic hexa-amine (23) may be synthesized by a simple alkylation procedure whereas the octa-amine (27) required a systematic stepwise synthesis.The hexa-amine salt (23)*6 HBr shows selectivity in forming inclusion complexes with the dicarboxylate anions (1-)O2C(CH2)nCO2(1-).
