Synthesis of substituted 2-phenylhistamines via a microwave promoted Suzuki coupling (original) (raw)
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The Journal of Organic Chemistry, 2013
A new route for the construction of 2aminoimidazolidines including analogues of the α 2 adrenergic agonist drug clonidine is elaborated. The key step is an intramolecular microwave-assisted Staudinger/aza-Wittig cyclization of an in situ generated urea intermediate (formed by the reaction of β-amino azide and isocyanate) upon treatment with Bu 3 P or polymer-supported phosphine reagent, allowing the introduction of various substituents at the N1 and the 2amino function. Furthermore, a useful one-pot Staudinger/aza-Wittig/Buchwald−Hartwig protocol leading to bicyclic guanidines has been elaborated.
Microwave-assisted regioselective N-alkylation of cyclic amidines
Tetrahedron Letters, 2007
A simple and efficient methodology for regioselective alkylation of exocyclic nitrogen of cyclic amidines was developed by microwave-assisted heating in the presence of amines. Novel N-alkylated 3,4-dihydropyrazino[2,1-b]quinazolin-6-ones were prepared in good yields. The reaction occurred via a transamination (addition-elimination) process involving a first attack of the amine on the electrophilic carbon of the amidine function.
Synthesis of Peptides Histamine H2 Receptors in Solid-Phase Assisted by Microwave Article
2020
Abstract: The synthesis of histamine H2 receptors peptides was conducted using the methodology of solid phase assisted by microwaves. Microwaves can reduce the reaction times during the coupling and deprotection steps to obtain the desired peptide sequence. The coupling reaction was carried out with a mixture of N,N′-diisopropylcarbodiimide (DIC) and N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU). The purity and yield are improved in peptide synthesis assisted by microwaves. Coupling reactions and deprotection on Rink resin were carried out in 5 min depending on amino acid and the length of the peptide chain.
Synthesis of amino-benzothiaoxazepine-1,1-dioxides utilizing a microwave-assisted, S(N)Ar protocol
ACS combinatorial science, 2011
The development of a microwave-assisted, intermolecular S(N)Ar protocol for the synthesis of a 126-member benzothiaoxazepine-1,1-dioxide library is reported. Diversification of 12 benzothiaoxazepine-1,1-dioxides was achieved in rapid fashion utilizing a variety of 2° amines and amino alcohols to generate an 80-member library. A second 48-member library was subsequently generated via a two-step alkylation, intermolecular S(N)Ar diversification protocol.
Microwave Assisted Synthesis: A New Technology in Drug Discovery
Mini-Reviews in Medicinal Chemistry, 2009
The interest in the microwave assisted organic synthesis has been growing during the recent years. It results from an increasing knowledge of fundamentals of the dielectric heating theory, availability of an equipment designed especially for the laboratory use as well as the discovery of the special techniques of the microwave syntheses. The efficiency of microwave flash-heating chemistry in dramatically reducing reaction times (reduced from days and hours to minutes and seconds) has recently been proven in several different fields of organic chemistry and this aspect is of great importance in high-speed combinatorial and medicinal chemistry. In this contribution, the current state of the art is summarized providing examples of the most recent applications in the field of microwave assisted synthesis of biologically active compounds both in heterocyclic and in peptide and peptidomimetic optimization.