Regioselective synthesis of new 2-(E)-cyano(oxazolidin-2-ylidene)thiazoles

Bakavoli, Mehdi; Beyzaei, Hamid; Rahimizadeh, Mohammad

doi:10.5155/eurjchem.2.3.356-358.389

Cited by 1 publication

(3 citation statements)

References 18 publications

(17 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the basis of our previously reported work [21], the thioamide itself was synthesized in a regioselective manner from functionalized oxazolidine with phosphorus pentasulfide.…”

Section: Resultsmentioning

confidence: 99%

“…and appropriate diaminoalkanes 2a-e (2 eq.) in absolute ethanol are refluxed for [16][17][18][19][20][21][22] 2c-e 4a-c …”

Section: Resultsmentioning

confidence: 99%

“…Monitoring of the progress of reactions and the purity of the products were effected by TLC on alufoil plates precoated with silica gel (60, Merck); eluent was CHCl 3 -CH 3 OH, 9 : 1, visualization with I 2 vapor. Compound 1 was obtained according to the published method [21]. (3a, b and 4a-c).…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives

Beyzaei

Aryan

Keshtegar

2014

Advances in Chemistry

Self Cite

View full text Add to dashboard Cite

Synthesis of new imidazolidine and tetrahydropyrimidine derivatives 3a, b and 4a-c as cyclic 1,3-diamines under two reaction conditions (A and B) is described. Under reaction conditions-A, a suspension of (E)-2-cyano-2-(oxazolidin-2-ylidene)ethanethioamide 1 (1 eq.) and diaminoalkanes 2a-e (2 eq.) in absolute ethanol is heated under reflux for 16-22 h to afford 3a, b and 4a-c. Alternatively, under reaction conditions-B, a solution of thioamide 1 (1 eq.) in diaminoalkanes 2a-e (3 eq.) is stirred under solvent-free conditions at room temperature for 3 days to give desired products. Reaction conditions-A for having higher yields, shorter reaction times, and required less diamines is more effective than reaction conditions-B. Oxazolidine ring opening is observed by reacting compound 1 with all of the diamines 2a-e, but the thioamide group only reacts with nonbulky diamines 2a, b. The chemical structures of novel compounds were confirmed by 1 H NMR, 13 C NMR, elemental analysis, and FT-IR spectrometry.

show abstract

“…On the basis of our previously reported work [21], the thioamide itself was synthesized in a regioselective manner from functionalized oxazolidine with phosphorus pentasulfide.…”

Section: Resultsmentioning

confidence: 99%

“…and appropriate diaminoalkanes 2a-e (2 eq.) in absolute ethanol are refluxed for [16][17][18][19][20][21][22] 2c-e 4a-c …”

Section: Resultsmentioning

confidence: 99%