1201683-08-0Relevant articles and documents
Tandem Copper-Catalyzed Regioselective N-Arylation-Aza-Michael Addition: Synthesis of Tetracyclic 5 H-Benzothiazolo[3,2- a]quinazoline Derivatives
Honnanayakanavar, Jyoti M.,Harish, Battu,Nanubolu, Jagadeesh Babu,Suresh, Surisetti
, p. 8780 - 8791 (2020/08/28)
A copper-catalyzed tandem process integrating regioselective N-arylation, followed by aza-Michael addition, is disclosed using 2-aminobenzothiazoles and ortho-halo cinnamic acid congeners. This process generated diverse tetracyclic 5H-benzothiazolo[3,2-a]quinazoline derivatives in moderate to good yields. The present tandem reaction appears to proceed through concomitant ring opening of 2-aminobenzothiazole and S-arylation to give the ortho-cyanamide-substituted diaryl thioether intermediate. The thus generated intermediate likely undergoes an unprecedented Truce-Smiles-type rearrangement involving S- to N-aryl migration, followed by reformation of the thiazole ring and intramolecular aza-Michael addition to furnish the title products.
Synthesis of 2-arylthio arylcyanamides from 2-iodoaryl isothiocyanates: Via a one-pot three-component reaction
Pinapati, Srinivasarao,Mandapati, Usharani,Tamminana, Ramana,Rudraraju, Rameshraju
, p. 8711 - 8713 (2017/08/29)
A one-pot three-component reaction has been described for the synthesis of substituted 2-arylthio arylcyanamides. A cheap and readily available iron source was used as a catalyst for this reaction. Consecutive addition and domino C-S cross-coupling reacti
Copper(I)-catalyzed cascade synthesis of 2-arylsulfanyl-arylcyanamides
Sahoo, Santosh K.,Jamir, Latonglila,Guin, Srimanta,Patel, Bhisma K.
scheme or table, p. 2538 - 2548 (2010/12/29)
We have developed a ligand-assisted copper(I)-catalyzed two sequential heteroarylation sequence. An intramolecular S-arylation is followed by an intermolecular N-arylation leading to the direct synthesis of N-aryl-2-aminobenzothiazoles. In most cases however, the 2-arylsulfanyl- arylcyanamide was the major product obtained via an intramolecular C-S bond formation, associated with C-S bond breakage, followed by an intermolecular S-arylation. The selectivity of this ligand-assisted reaction is quite different as compared to that of ligand-free reactions and the rates are much faster giving good yields of products. Various cyanamides can be prepared in excellent yields from their corresponding 1-substituted thioureas with or without the assistance of a ligand with a catalytic quantity of copper(I).
