Reaction of Hydrazonoyl Halides 55¹: Synthesis of 2,3-Dihydro[1,3,4]-Thiadiazoles Containing Steroid Moiety

Abstract

4-thiadiazolylsteroids were synthesized from the appropriate hydrazonoyl halides and alkyl carbodithioates containing steroid moiety. The newlysynthesized compounds were elucidated by elemental analysis, spectral data, and alternative synthetic route whenever possible.

Reactions with hydrazonoyl halides 66: Synthesis of some new 1,3,4-thiadiazoles, triazolino[4,3-a]pyrimidines and isoxazolo[3,4-d]pyridazines containing coumarin moiety

“…Elemental analyses were carried out at the Microanalytical Center of Cairo University. Hydrazonoyl halides [16,[17][18][19], 2-acetylbenzo[f]2H-chromen-3-one [20], 3-(2-bromoacetyl)-2H-chromen-2-one [21] and alkyl carbodi-thioates [22] were prepared as previously reported.…”

“…Method A: A mixture of the hydrazonoyl bromide, 1, (1.86 g, 5 mmol) and the appropriate of pyrimidine-2-thione derivatives [23] 8a-f, 2-thioxo-2,3-dihydro-1H-quinazolin-4one, 2-thioxo-2,3,5,6,7,8-hexahydro-1H-benzo [4,5] Method B: A mixture of the appropriate hydrazonoyl bromide, 1 (1.68 g, 5 mmol), the appropriate of 14a-e [22] (5 mmol), and sodium ethoxide (0.34 g, 5 mmol) in ethanol (20 mL) was refluxed for 3 hrs. The reaction mixture was cooled and the resulting solid was collected and crystallized from the proper solvent gave products identical in all aspects (m.p., mixed m.p., and spectra) with corresponding products obtained by Method A.…”

1,3,4-Thiadiazoles of pharmacological interest: Recent trends in their synthesis via tandem 1,3-dipolar cycloaddition: Review

“…The steroidal dithiocarbazates 82A , B were also reported to undergo similar reaction with hydrazonoyl halides II , VII , IX , XI, and XII and gave the respective 1,3,4-thiadiazoles 83A , B ( Scheme 46 ) [82] .…”

“…Likewise, 2,3-dihydro-1,3,4-thiadiazolyl steroids 80 were analogously prepared in 60–68% yields by reaction of alkyl dithiocarbazate 79 with various hydrazonoyl halides II , VII , IX , XI, and XII under the same reaction conditions ( Scheme 44 ) [82] .…”