Synthesis of Sulfur-Containing Heterocycles through Oxidative Carbon–Hydrogen Bond Functionalization

Abstract

Vinyl sulfides react rapidly and efficiently with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form α,β-unsaturated thiocarbenium ions through oxidative carbon–hydrogen bond cleavage. These electrophiles couple with appended π-nucleophiles to yield sulfur-containing heterocycles through carbon–carbon bond formation. Several nucleophiles are compatible with the procedure and the reactions generally proceed through readily-predictable transition states.

A Radical Reaction for the Synthesis of 3‐Substituted Dihydrothiopyrans under Photosensitized Conditions

“…Several approaches can be used for the synthesis of S‐containing heterocycles, including thia‐Prins cyclization, Michael/aldol reaction, thionium–ene cyclization reaction, oxidative C−H bond functionalization, and so forth . In this context, a novel approach was proposed using radical reactions because it is well known that radical reactions show different reactivity and selectivity compared with ordinary ionic reactions .…”

Convergent One-Pot Oxidative [n + 1] Approaches to Spiroacetal Synthesis

“…The formation of 27 is remarkable because the cyclization occurs in preference to allylic alcohol oxidation. 26 The construction of 28 and 29 shows that dihydropyrans containing tertiary benzylic alcohols are excellent substrates, illustrating the promise of this protocol to deliver structurally diverse products. The scope of this process can be expanded through the use of a broader range of nucleophiles and by retention of oxygenation during the fragment-coupling stage.…”

Simple synthesis of new imidazopyridinone, pyridopyrimidinone, and thiazolopyridinone derivatives and optimization of reaction parameters using response surface methodology

“…[1][2][3][4][5][6] Nitrogen and sulfur containing heterocyclic compounds broadly exist in various natural and synthetic products, and play vital roles in medicinal chemistry. [7][8][9][10] Among these heterocycles, pyridine derivatives, such as imidazopyridine, pyridopyrimidine, and thiazolopyridine derivatives have received considerable attention over the past years due to their diverse biological activities and clinical applications. 11,12 Imidazopyridine derivatives have shown a broad range of interesting biological activities, such as antifungal, antitumor, antiviral, antibacterial, anti-HIV, 13 antipyretic, analgesic, hypnoselective, anxioselective, anti-inammatory, anticonvulsant, antiulcer, immunomodulatory 14 activities; also pyridopyrimidine derivatives 15 are found to exhibit a broad spectrum of potent antibacterial, antiallergic, antimicrobial, 12 anti-inammatory, analgesic, 16,17 tyrosine kinase, calcium channel antagonists, 8,18 tuberculostatic, antileishmanial, antitumor, 19 antifolate, antihypertensive, hepatoprotective, 20 anticancer 21 properties; and thiazolopyridine derivatives are associated with a wide range of biological activities such as analgesic, antioxidant, 11 anticancer, 22 anti-inammatory, 23 antihypertensive, 24 antibacterial, and antifungal 25,26 properties.…”