REGIOSPECIFIC SYNTHESIS OF A NEW CHIRAL <i>N</i>-SUBSTITUTED PYRAZOLE USING A SESQUITERPENE HYDROCARBON

Auhmani, Aziz; Kossareva, E.; Eljamili, H.; Réglier, Marius; Pierrot, M.; Benharref, Ahmed

doi:10.1081/scc-120002507

Cited by 22 publications

(16 citation statements)

References 9 publications

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“…The use of a palladium‐based method also proved unfruitful with this system 31. Despite its successful use in related cases, the N ‐bromosuccinimide (NBS) based method32 only resulted in electrophilic substitution of the alkene. The use of t BuOOH in the presence of copper catalysts33 yielded an unidentifiable product.…”

Section: Methodsmentioning

confidence: 99%

Diversity‐Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis

Valot¹,

García²,

Duplan³

et al. 2012

Angew Chem Int Ed

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Section: Methodsmentioning

confidence: 99%

Diversity‐Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis

Valot¹,

García²,

Duplan³

et al. 2012

Angew Chem Int Ed

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“…Thus, treatment of thiosemicarbazone 1 (Auhmani et al, 1999(Auhmani et al, , 2002Ourhriss et al, 2005) or thiosemicarbazone 2 with an equivalent of ethyl 2-bromoacetate in the presence of sodium acetate afforded the nonsubstituted thiazolidinones (Z)-2-{(Z)-[(1aR,5aR,9aS)-1,1-dichloro-1a,5,5,7-tetramethyl-1a,2,3,4,5,5a,8,9-octahydro-1H-benzo[a]cyclopropa[b][7]annulen-8-ylidene]hydrazono}thiazolidin-4-one, 3, and (Z)-2-{(Z)-[(1aR,5aR,9aS)-1,1-dibromo-1a,5,5,7-tetramethyl-1a,2,3,4,5,5a,-8,9-octahydro-1H-benzo[a]cyclopropa[b][7]annulen-8-ylidene]-hydrazono}thiazolidin-4-one, 4. They were purified by flash chromatography with hexane as eluent and isolated as yellow liquids.…”

Section: Synthesismentioning

confidence: 99%

Hemisynthesis, crystal structure and inhibitory effect of sesquiterpenic thiosemicarbazones and thiazolidin-4-ones on the corrosion behaviour of stainless steel in 1 M H₂SO₄ solution

Bimoussa¹,

Koumya

Abouelfida

et al. 2019

Acta Crystallogr C Struct Chem

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Treatment of thiosemicarbazones prepared from sesquiterpenes with ethyl 2‐bromoacetate in the presence of sodium acetate afforded the corresponding thiazolidin‐4‐ones. The structures of all the newly synthesized compounds were established by considering spectral and single‐crystal X‐ray diffraction data. The title compound, ethyl 2‐((Z)‐2‐{(Z)‐[(1aR,5aR,9aS)‐1,1‐dichloro‐1a,5,5,7‐tetramethyl‐1a,2,3,4,5,5a,8,9‐octahydro‐1H‐benzo[a]cyclopropa[b][7]annulen‐8‐ylidene]hydrazono}‐4‐oxothiazolidin‐3‐yl)acetate, C23H31Cl2N3O3S, 5, crystallizes in the orthorhombic noncentrosymmetric space group P212121 with Z = 4. Within the molecule in the crystal structure, the cyclohexene ring has an envelope conformation and the cycloheptane ring, to which it is fused, has a boat conformation. In the crystal, molecules are linked by C—H…Cl hydrogen bonds forming chains propagating along the b‐axis direction. The absolute configuration of the molecule in the crystal could be fully confirmed from anomalous dispersion effects [Flack parameter = −0.04 (2)]. Thiosemicarbazones 1 and 2 are efficient inhibitors for steel corrosion in 1 M H2SO4 solution, with a maximum efficiency of 92.28% at 10−3 M. Furthermore, thiosemicarbazone compounds were found to be more efficient than thiazolidin‐4‐one derivatives. In addition, cyclic voltammetry was used to characterize the tested molecules, as well to estimate the experimental value of the energy band gap.

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“…The essential cedar oil is mainly composed of sesquiterpene hydrocarbons with notable olfactory and important biological properties. In fact, many different methods for functionalization of this essential oil have been developed in order to prepare new products having olfactory properties suitable for the perfume, cosmetics or insecticides industries (Auhmani et al, 2002;Eljamili et al, 2002). In order to prepare new products with added value using sesquitertpene hydrocarbons isolated from essential cedar oil, we synthesized the title compound in two steps from -himachalene.…”

Section: Structure Descriptionmentioning

confidence: 99%

(1S,3R,8R,11S)-2,2,11-Tribromo-10-bromomethyl-3,7,7-trimethyltricyclo[6.4.0.0^1,3]dodec-9-ene

Bimoussa¹,

Auhmani²,

Itto³

et al. 2016

IUCr Data

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The title compound, C16H22Br4, was synthesized in two steps from β-himachalene, which was isolated from essential oil of the Atlas cedar (cedrus atlantica). It is built up from three fused rings, a seven-membered heptane ring, a six-membered cyclohexyl ring bearing both a bromine and a bromomethyl substituent, and a three-membered propane ring bearing two Br atoms. In the crystal, molecules are linked by C—H...Br hydrogen bonds, forming chains propagating along [001]. The absolute configuration was deduced from the chemical pathway and confirmed by resonant scattering [Flack parameter = 0.012 (10)].

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REGIOSPECIFIC SYNTHESIS OF A NEW CHIRAL N-SUBSTITUTED PYRAZOLE USING A SESQUITERPENE HYDROCARBON

Cited by 22 publications

References 9 publications

Diversity‐Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis

Diversity‐Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis

Hemisynthesis, crystal structure and inhibitory effect of sesquiterpenic thiosemicarbazones and thiazolidin-4-ones on the corrosion behaviour of stainless steel in 1 M H₂SO₄ solution

(1S,3R,8R,11S)-2,2,11-Tribromo-10-bromomethyl-3,7,7-trimethyltricyclo[6.4.0.0^1,3]dodec-9-ene

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REGIOSPECIFIC SYNTHESIS OF A NEW CHIRAL N-SUBSTITUTED PYRAZOLE USING A SESQUITERPENE HYDROCARBON

Cited by 22 publications

References 9 publications

Diversity‐Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis

Diversity‐Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis

Hemisynthesis, crystal structure and inhibitory effect of sesquiterpenic thiosemicarbazones and thiazolidin-4-ones on the corrosion behaviour of stainless steel in 1 M H2SO4 solution

(1S,3R,8R,11S)-2,2,11-Tribromo-10-bromomethyl-3,7,7-trimethyltricyclo[6.4.0.01,3]dodec-9-ene

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Hemisynthesis, crystal structure and inhibitory effect of sesquiterpenic thiosemicarbazones and thiazolidin-4-ones on the corrosion behaviour of stainless steel in 1 M H₂SO₄ solution

(1S,3R,8R,11S)-2,2,11-Tribromo-10-bromomethyl-3,7,7-trimethyltricyclo[6.4.0.0^1,3]dodec-9-ene