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Synthesis of S-Heterocycles

Synthesis of      

benzo-fused
S-Heterocycles
     

Cyclic Sulfides
     

Thioacetals

Oxathioacetals

Sultams

Thiazolines

Thiophenes

Thiazoles
Benzothiazoles

Isothiazoles
 

1,3,4-
Thiadiazoles

1,2,4-
Thiadiazoles
   

Protecting Groups


1,3-Dithianes, 1,3-Dithiolanes


Recent Literature


An efficient reaction of carbon disulfide with oxiranes in the presence of sodium hydride (10 mol%) and methanol gives functionalized 1,3­oxathiolane-2-thiones in very good yields.
I. Yavari, M. Ghazanfarpour-Darjani, Z. Hossaini, M. Sabbaghan, N. Hosseini, Synlett, 2008, 889-891.


A highly efficient and stereoselective gold-catalyzed cycloisomerization of α-thioallenes to 2,5-dihydrothiophenes has been discovered.
N. Morita, N. Krause, Angew. Chem. Int. Ed., 2006, 45, 1897-1899.


A rhodium-catalyzed transannulation of 1,2,3-thiadiazoles with aliphatic, aromatic, and heteroaromatic alkenes enables a regioselective synthesis of a wide range of dihydrothiophenes. A subsequent addition of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) provides thiophenes. The present method offers broad substrate scope, wide functional group compatibility, and high regioselectivity.
J.-Y. Son, J. Kim, S. H. Han, S. H. Kim, P. H. Lee, Org. Lett., 2016, 18, 5408-5411.


With CuI as the catalyst and K3PO4 • 3 H2O as the base, a highly efficient, ligand-free intramolecular S-vinylation of thiols with vinyl chlorides or bromides was successfully implemented. Moreover, competition experiments revealed that the 4-exo cyclization is fundamentally preferred over other modes (5-exo, 6-exo, and 6-endo) of cyclization.
Q. Zhao, L. Li, Y. Fang, D. Sun, C. Li, J. Org. Chem., 2009, 74, 459-462.


The reaction of 3-sulfolene with arylboronic acids in the presence of a chiral diene-rhodium catalyst under highly basic conditions gave high yields of 3-arylsulfolanes with high enantioselectivity via a base-catalyzed isomerization to the more reactive 2-sulfolene.
K. M.-H. Lim, T. Hayashi, J. Am. Chem. Soc., 2015, 137, 3201-3204.


A facile and practical TBAI-catalyzed reaction between N-tosyl hydrazones and sulfur provides 1,2,3-thiadiazoles in good yields under metal-free conditions. This procedure serves as an improvement for the Hurd-Mori reaction.
J. Chen, Y. Jiang, J.-T. Yu, J. Cheng, J. Org. Chem., 2016, 81, 271-275.


A three-component condensation gave 2-amino-4H-1,3-oxazines or 2-amino-4H-1,3-thiazines from alkynes, urea or thiourea, and aldehydes.
S. Huang, Y. Pan, Y. Zhu, A. Wu, Org. Lett., 2005, 7, 3797-3799.