The Reaction of N-Isocyaniminotriphenylphosphorane with 2-Oxopropylbenzoate (or 4-Bromobenzoate) and a Primary Amine in the Presence of (E)-Cinnamic Acid Derivatives: A One-Pot Efficient Four-Component Reaction for the Synthesis of 2-(Arylamino)-2-(5-aryl

Ramazani, Ali; Ahmadi, Yavar; Nasrabadi, Fatemeh Zeinali; Rouhani, Morteza

doi:10.1002/jhet.1563

Cited by 7 publications

(7 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Substituted benzyldehydes, 95,101 aromatic dialdehydes, 110 furfural, 111 acetaldehyde, 96,97 and cinnamaldehyde 106,112 readily react as carbonyl components. On the other hand, ketones are restricted to be cyclic 103,113−117 or electron-deficient α-halo ketones, 108,118 α-acyl(thi)oxy propanones, 98,99,107,119 and biacetyl. 100 The mechanism proposed for the Ramazani-4CR comprises the initial steps of the classic Ugi-4CR, that is, the formation of the protonated the iminium ion 44, which subsequently adds to isonitrile 1 along with the carboxylate anion to form the corresponding α-adduct 45.…”

Section: Reactionsmentioning

confidence: 99%

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

et al. 2020

View full text Add to dashboard Cite

N-Isocyaniminotriphenylphosphorane (NIITP) is a functionalized isonitrile that has been extensively applied in a variety of organic reactions during the last two decades. This Review summarizes the most important applications in organic synthesis of this versatile reactant, with the focus posed on mechanistic and methodological aspects allowing the generation of molecular diversity. NIITP combines the reactivity of isonitriles with that of phosphoranes to enable chemical transformations employed in the construction of compound libraries. Here, we cover from the initial applications of NIITP in the Nef isocyanide reaction to further derivations that render a variety of heterocyclic scaffolds. The presence of the isonitrile moiety in this singular compound makes possible the double addition of nucleophiles and electrophiles, which followed by inter(intra)molecular aza-Wittig type transformations enable several multicomponent and tandem processes. In particular, we stress the impact of NIITP in oxadiazole chemistry, from the early two-component transformations to recent examples of multicomponent reactions that take place in the presence of suitable electrophiles. In addition, we briefly describe the role of NIITP chemistry in generating skeletal and conformational diversity in cyclic peptides. The reaction of NIITP with alkynes is thoroughly revised, with particular emphasis on silver-catalyzed processes that have been developed in the last years. Biomedicinal applications of some reaction products are also mentioned along with a perspective of future applications of this reactant.

show abstract

Section: Reactionsmentioning

confidence: 99%

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Recently, we have established a one-pot method for the synthesis of organophosphorus compounds [17][18][19]. We have reported the regioselective and stereoselective preparation of electron-poor N-vinyl tetrazoles from the acetylenic esters and 5-benzyl-2H-tetrazole in the presence of triphenylphosphine and the structure of one of the products, namely compound ethyl-(Z)-3-phenyl-2-(5-phenyl-2H-1,2,3,4-tetraazol-2-yl)-2-propenoate was confirmed by single-crystal X-ray analysis [20].…”

Section: P a G E | 34mentioning

confidence: 99%

Molecular Structure, NMR, FMO, MEP and NBO Analysis of ethyl-(Z)-3-phenyl-2-(5-phenyl-2H-1,2,3,4-tetraazol-2-yl)-2-propenoate Based on HF and DFT Calculations

2017

Self Cite

View full text Add to dashboard Cite

In the present work, for the first time the quantum calculations of Ethyl-(Z)-3-phenyl-2-(5-phenyl-2H-1,2,3,4-tetraazol-2-yl)-2-propenoate are evaluated using the HF and B3LYP methods with 6-311++G** basis set. The geometry of the title compound was optimized by B3LYP/6-311++G** level of theory. The theoretical 1 H and 13 C NMR chemical shift values of the title compound are calculated and compared with the experimental results. The computed data are in good agreement with the experimental data. Frontier molecular orbitals (FMOs), molecular electrostatic potential (MEP), energy gap between HOMO and LUMO, electronic properties, thermodynamic parameters, natural charges distribution (NBO charges) and NBO analysis were investigated and discussed by theoretical calculations. KEYWORDSTetrazole DFT natural charge NBO analysis electronic properties Graphical AbstractMolecular structure, NMR, FMO… P a g e | 33

show abstract

“…One of the main challenges in medicinal chemistry is the design and synthesis of biologically active molecules. Multicomponent reactions, due to their valued features such as simple procedures, atom economy, facile execution, and the opportunity to construct target compounds by the introduction of several diversity elements in a single chemical event, are one of the best tools in the synthesis of diverse and complex compounds as well as small and drug‐like heterocycles . Of pivotal importance in this area are the azaaromatic‐acetylenedicarboxylate zwitterions, which are easily generated by the addition of azaaromatic compounds such as pyridines and isoquinolines to acetylenedicarboxylates.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Synthesis of Regioselective Polysubstituted Indolizines via Three‐Component Reactions of Dialkyl Acetylendicarboxylates, Dialkylchloro Malonates, and Pyridines

Piltan

Kalantari

2016

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

The Reaction of N-Isocyaniminotriphenylphosphorane with 2-Oxopropylbenzoate (or 4-Bromobenzoate) and a Primary Amine in the Presence of (E)-Cinnamic Acid Derivatives: A One-Pot Efficient Four-Component Reaction for the Synthesis of 2-(Arylamino)-2-(5-aryl

Cited by 7 publications

References 44 publications

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

Molecular Structure, NMR, FMO, MEP and NBO Analysis of ethyl-(Z)-3-phenyl-2-(5-phenyl-2H-1,2,3,4-tetraazol-2-yl)-2-propenoate Based on HF and DFT Calculations

One‐Pot Synthesis of Regioselective Polysubstituted Indolizines via Three‐Component Reactions of Dialkyl Acetylendicarboxylates, Dialkylchloro Malonates, and Pyridines

Contact Info

Product

Resources

About