We disclose a method using phenyl
isocyanate to synthesize carbonyl-containing N-heterocycles.
The metal-free novel approach for both N–H
and C–H carbonylation processes was successfully refined, delivering
a range of synthetically valuable derivatives of quinazoline-2,4(1H,3H)-dione, 2H-benzo[e] [1,2,4] thiadiazin-3(4H)-one 1,1-dioxide,
and pyrrolo[1,2-a] quinoxalin-4(5H)-one. The protocol features broad substrates with diverse reactions
suitable for excellent yields, mild conditions, and good functional
group compatibility. Moreover, the applicability of the reaction was
characterized by gram-scale synthesis and synthetic transformations
for drug molecules.
A new and efficient strategy for the development of quinazolinones and dihydroquinazolin-4(1H)-ones promoted by ammonium thiocyanate is reported. Most remarkably, dimethyl sulfoxide is used for solvent as well as methine and bridged methylene source to obtain a wide variety of new N, N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones. This transformation possesses significant advantages such as metal-and oxidant-free, non-acidic medium, simple condition, good functional group tolerance and broad substrate scope. Besides, this process could be readily scaled up and applied to drug molecules synthesis.
This study described an efficient synthesis of disulfide from two thiols in a continuous flow reactor, using 1-chlorobenzotriazole (BtCl) as an oxidant. It has been demonstrated that this method is feasible with a variety of aliphatic and aromatic thiols to produce a corresponding disulfide under mild conditions. Productivity of this process is determined by a high yield, a wide range of functional group compatibility, and the fact that disulfide is readily available in a short timeframe. This method enables the simple synthesis of a series of symmetrical and unsymmetrical disulfides.
N,N-Dialkyl amides such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA), are common polar solvents, finds application as a multipurpose reagent in synthetic organic chemistry. They are cheap, readily available and versatile synthons that can be used in a variety of ways to generate different functional groups. In recent years, many publications showcasing, excellent and useful applications of N,N-dialkyl amides in amination (R-NMe 2 ), formylation (R-CHO), as a single carbon source (R-C), methylene group (R-CH 2 ), cyanation (R-CN), amidoalkylation (-R), aminocarbonylation (R-CONMe 2 ), carbonylation (R-CO) and heterocycle synthesis appeared. This chapter highlights important developments in the employment of N,N-dialkyl amides in the synthesis of heterocycles and functionalization of acyclic systems. Although some review articles covered the application of DMF and/or DMA in organic functional group transformations, there is no specialized review on their application in the synthesis of cyclic and acyclic systems.
We herein promote a simple copper-catalyzed assembly to formulate quinazoline and indazolone derivatives in a single protocol manner. These transformations are based on that DMF can serve as reaction solvents and one carbon synthon for the construction of heterocyclic ring. Moreover, this protocol features with base and Bronsted acid free, environmentally benign, broad synthetic scope and scalability is demonstrated.
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