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Synthesis of S-Heterocycles

Synthesis of      

benzo-fused
S-Heterocycles
     

Cyclic Sulfides

Thioacetals

Oxathioacetals
 

Sultams

1,3-Thiazolidine-2-thiones
   

Thiazolines
     

Thiophenes

Thiazoles
Benzothiazoles

Isothiazoles
 

1,3,4-
Thiadiazoles

1,2,4-
Thiadiazoles

1,2,3-
Thiadiazoles
 

Protecting Groups


1,3-Dithianes, 1,3-Dithiolanes


Recent Literature


Two complementary paths enable the synthesis of 3,4-disubstituted thietes in good yields via α-metalation or direct C-H functionalization.
M. Eisold, A. Müller-Deku, F. Reiners, D. Didier, Org. Lett., 2018, 20, 4654-4658.


Efficient acyl thiol-ene (ATE) or acyl thiol-yne (ATY) cyclization convert unsaturated thiocarboxylic acid derivatives into thiolactones in very good yields under mild conditions. The reactions offer high diastereoselectivity, excellent regiocontrol, and broad substrate scope.
R. O. McCourt, F. Dénès, G. Sanchez-Sanz, E. M. Scanlan, Org. Lett., 2018, 20, 2948-2951.


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 visible light-promoted three-component tandem annulation of α-bromoesters, amines, and aryl/alkyl isothiocyanates provides 2-iminothiazolidin-4-ones at room temperature in the absence of metal and photocatalyst. This [1 + 2 + 2] cyclization strategy offers broad substrate scope, excellent functional group tolerance, mild reaction conditions, step-economy, and simple operation.
W. Guo, M. Zhao, W. Tan, L. Zheng, K. Tao, L. Liu, X. Wang, D. Chen, X. Fan, J. Org. Chem., 2018, 83, 1402-1413.


A molecular iodine-catalyzed oxidative cyclization of 2-aminopyridine/amidine and isothiocyanate via N-S bond formation enables the synthesis of N-fused and 3,4-disubstituted 5-imino-1,2,4-thiadiazole derivatives at ambient temperature. This transition-metal-free protocol provides a facile and highly efficient regiospecific synthesis of various 1,2,4-thiadiazole derivatives with good to excellent yields using inexpensive I2 as a catalyst.
N. Tumula, N. Jatangi, R. K. Palakodety, S. Balasubramanian, M. Nakka, J. Org. Chem., 2017, 82, 5310-5316.


A facile and scalable synthesis of δ-thiolactones from inexpensive and readily available γ-unsaturated esters incorporates a radical acyl thiol-ene reaction as the key C-S bond forming step. Cyclization is achieved via a Steglich-type thiolactonization of 5-mercaptopentanoic acids.
R. O. McCourt, E. M. Scanlan, Org. Lett., 2019, 21, 3460-3464.


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.