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When a ligand binds to a cell-surface receptor, the receptor's intracellular domain changes shape, which may either activate its enzyme function or allow its binding to other molecules. The initial signal is amplified by most signal transduction pathways. This means that a single ligand molecule can activate multiple molecules of a downstream target. Proteins that relay a signal are most commonly phosphorylated at one or more sites, activating or inactivating the protein. Kinases catalyze...
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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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A novel [5 + 1 + 3] cascade cyclization efficiently synthesizes benzo[4,5]thieno[3,2-d]pyrimidine derivatives. This method uses readily available starting materials, offering a versatile route to diverse compounds.

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Area of Science:

  • Organic Chemistry
  • Heterocyclic Chemistry
  • Synthetic Chemistry

Background:

  • Benzo[4,5]thieno[3,2-d]pyrimidine scaffolds are important in medicinal chemistry.
  • Efficient synthetic routes to these heterocycles are highly sought after.

Purpose of the Study:

  • To disclose a novel cascade cyclization reaction.
  • To develop an efficient synthesis for benzo[4,5]thieno[3,2-d]pyrimidine derivatives.

Main Methods:

  • Reaction of o-nitrochalcones with elemental sulfur and guanidine.
  • Base-promoted cyclization in ethanol.
  • One-pot reaction procedure.

Main Results:

  • Successful synthesis of structurally diverse benzo[4,5]thieno[3,2-d]pyrimidines.
  • High yields ranging from 77-89%.
  • Wide substrate compatibility demonstrated with 33 examples.

Conclusions:

  • The developed [5 + 1 + 3] cascade cyclization is an effective method for preparing benzo[4,5]thieno[3,2-d]pyrimidines.
  • The protocol is efficient, high-yielding, and versatile, making it valuable for synthetic chemists.