A Facile One-Pot Synthesis of 1-Substituted Tetrazole-5-thiones and 1-Substituted 5-Alkyl(aryl)sulfanyltetrazoles from Organic Isothiocyanates

Abstract

Treatments of organic isothiocyanates (R-NCS) with NaN 3 in the presence of pyridine in water at room temperature gave corresponding various organic tetrazole-thiones, [S=CN 4 (R)] (R = alkyl or aryl). Isolated products are obtained as white or yellow solids in good yields (76-97%). The molecular structure by X-ray diffraction study for one of products shows the proposed formation. In addition, one-pot synthesis of 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles has been demonstrated. Addition of alkyl or aryl halides into the mixture of organic isothiocyanates, NaN 3 , and pyridine in water at room temperature exclusively formed 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles (S-derivatives) in high yields.

Facile formation of tetrazole–thiolato Pd(ii) and Pt(ii) complexes through deprotonation or oxidative addition using organic tetrazole–thiones

“…We prepared 1-(2-methallyl)-1 H -tetrazole-5-thione ( 22 , {S[CN 4 H(R)]} (R = 2-methallyl)) using a similar literature process 43 to determine whether the hydrogen migrates to position-1 or -2 of the olefinic bond when the allyl group is substituted (Scheme 10). We then reacted Pt(styrene)L 2 (L = PMe 3 ) with organic tetrazole–thione 22 .…”

Synthesis of Some Derivatives of Pyrimido[5,4-e]Tetrazolo[5,1-c][1,2,4]triazine; a Novel Heterocyclic System

“…The starting material, 1-phenyl-5-methylsulfanyltetrazole 1 was easily obtained from the treatment of phenyl isothiocyanate with NaN 3 in the presence of pyridine in water at room temperature and subsequent methylation with methyl iodide. 26 The reaction of compound 1 with hydrazine hydrate gave, quantitatively, the desired hydrazine derivative 2 which has been synthesised previously with modifications, but not completely characterised. [27][28][29] On the other hand, 5-bromo-2,4-dichloro-6-methylpyrimidine 3 was prepared through the reaction of thiourea and ethyl acetoacetate in a four-stage method.…”

Visible-Light-Induced Organophotocatalytic Difunctionallization: Open-Air Hydroxysulfurization of Aryl Alkenes with Aryl Thiols

“…All substrates 2a – 2j were commercially available. Substrates 2k – 2o were prepared by the following representative procedure . To a 100 mL two-neck round-bottom flask were added 4-bromophenyl isothiocyanate (535.2 mg, 2.5 mmol) and 25% H 2 O/ i -PrOH (10 mL).…”

“…Substrates 2k−2o were prepared by the following representative procedure. 17 To a 100 mL two-neck round-bottom flask were added 4-bromophenyl isothiocyanate (535.2 mg, 2.5 mmol) and 25% H 2 O/i-PrOH (10 mL). Then, sodium azide (243.8 mg, 3.75 mmol, 1.5 equiv) was added to the reaction mixture and stirred at reflux.…”