Synthesis, crystal structure of some new 2‐(4‐methylbenzoylimino)‐3‐aryl‐4‐methyl‐1,3‐thiazolines

Saeed, Aamer; Parvez, Masood

doi:10.1002/jhet.5570430431

Cited by 23 publications

(14 citation statements)

References 22 publications

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“….362(5) Åagree with the literature reports [21][22][23][24][25]. The bond length d(C14-N2) =1.259(5) Åand the angles ÐN2-C14-S2 =128.2(3)°and ÐN2-C14-N1 =121.8(4)°con-firm the imine nature of the N2-C14 bond.…”

Section: Discussionsupporting

confidence: 53%

“…The packing in the title crystal structure can be described as asuccessionofparallel layers.The conjugationbetween C=Oand the amiden itrogeni se vident from thev alue of theb ondl ength d(Nl-C10) =1.362(5)Å.The thiazole ring is planar as indicated by torsion angles ÐC9-C10-N1-C14 =-3.4(5)°, ÐN1-C10-C9-S2 =0.4(4)°, ÐC10-C9-S2-C14 =1.8(3)°and ÐN1-C14-S2-C9 =-36(3)°. In addition, the torsion angles ÐS2-C14-N2-C15 =0 .8(6)°, ÐO1-C10-N1-C11 =1 .2(6)°, ÐN2-C14-N1-C11 =1.8(6)°, ÐC5-C8-C9-S2 =-1.0(7)°and ÐN1-C10-C9-S2 =0 .4(4)°revealed that the thiazole ring is coplanar with O1, N2,C 5, C8,C 11 and C15.T he distances.362(5) Åagree with the literature reports [21][22][23][24][25]. The bond length d(C14-N2) =1.259(5) Åand the angles ÐN2-C14-S2 =128.2(3)°and ÐN2-C14-N1 =121.8(4)°con-firm the imine nature of the N2-C14 bond.…”

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confidence: 64%

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Crystal structure of (2Z,5Z)-3-allyl-5-(4-(methylthio)benzylidene)- 2-(p-tolylimino)thiazolidin-4-one, C21H20N2OS2

Mamaghani¹,

Joshari²,

Tabatabaeian³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialTo as olution of 3-allyl-2-(p-tolylimino)thiazolidin-4-one (3 mmol) and base supported ionic liquid-like phase (SILLP) (0.5 g) in ethanol (20 mL), 4-methylthiobenzaldehyde (3 mmol) was added and the mixture was heated at reflux for 3h.S ILLP was separated by filtration. Then the solution was concentrated in vacuum and kept at -15 ºC over 2h.The residue was filtered off and recrystallized from methanol to give 3-allyl-5-(4-(methylthio)benzylidene)-2-(p-tolylimino)thiazolidin-4-one as ayellow solid in 87 %yield (m.p. =138-140°C). Elemental analysisfound: C, 66.13 %; H, 5.35 %; N, 7.47 %; calculated for C 21 H 20 N 2 OS 2 :C,66.28 %; H, 5.30 %; N, 7.36 %. Melting points were measured on aElectrothermal 9100 instrument and are uncorrected. Elemental analyses were made by aC arlo-Erba EA1110CNNO-S analyzer. Experimental detailsAll hydrogen atomswere refined in isotropic approximation in a riding model with U iso (H) =1 .2 U eq (C). The structure was checked with PLATON [1] and no solvent accesible void was found. The residual densities are 0.32 eÅ -3 (highest peak at 1.24 Åfrom C13) and -0.21 eÅ -3 (deepest hole at 0.61 Åfrom H12). DiscussionThiazolidinone moiety is an important structure element in medicinal chemistry [2][3][4][5][6] and substituted thiazolidinones show a broad spectrum of biological activities [7][8][9][10][11] [16].Therefore, facile preparation of various 5-arylidene thiazolidinones is highly desirable. In continuation of our ongoing interests in the development of benign methods targeted at the synthesis of biologically important heterocycles [17][18][19], we used base supported ionic liquid-like phase (SILLP) [20] as an efficientand recyclablesolid phasecatalystinthe synthesis of thetitle compound. The X-ray diffractometric analysis of the title product was carried out on the single crystal prepared in peteroleum ether/EtOAc(4:1). The packing in the title crystal structure can be described as asuccessionofparallel layers.The conjugationbetween C=Oand the amiden itrogeni se vident from thev alue of theb ondl ength d(Nl-C10) =1.362(5)Å.The thiazole ring is planar as indicated by torsion angles ÐC9-C10-N1-C14 =-3.4(5)°, ÐN1-C10-C9-S2 =0.4(4)°, ÐC10-C9-S2-C14 =1.8(3)°and ÐN1-C14-S2-C9 =-36(3)°. In addition, the torsion angles ÐS2-C14-N2-C15 =0 .8(6)°, ÐO1-C10-N1-C11 =1 .2(6)°, ÐN2-C14-N1-C11 =1.8(6)°, ÐC5-C8-C9-S2 =-1.0(7)°and ÐN1-C10-C9-S2 =0 .4(4)°revealed that the thiazole ring is coplanar with O1, N2,C 5, C8,C 11 and C15.T he distances.362(5) Åagree with the literature reports [21][22][23][24][25]. The bond length d(C14-N2) =1.259(5) Åand the angles ÐN2-C14-S2 =128.2(3)°and ÐN2-C14-N1 =121.8(4)°con-firm the imine nature of the N2-C14 bond. The distance d(C8-C9)=1.331(5) Åand the angles ÐC8-C9-S2 =129.7(3)°a nd ÐC8-C9-C10 =120.5(3)°are consistant with double bond features of C8-C9.This analysis also unambiguously confirmed the Z configuration at the chiral axis and this is quite evident from the spatial orientation of arylg roups attached to C14-N2 and C8-C9 double bonds.

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Section: Discussionsupporting

confidence: 53%

supporting

confidence: 64%

Crystal structure of (2Z,5Z)-3-allyl-5-(4-(methylthio)benzylidene)- 2-(p-tolylimino)thiazolidin-4-one, C21H20N2OS2

Mamaghani¹,

Joshari²,

Tabatabaeian³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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“…There are two kinds of hydrogen bonds N-H···Br and Br···H-O-H( figure, top). The bond dis- (2) Å are in the range reported in the literature [14][15][16][17]. The thiazole ring is planer as indicated with torsion angles ∠C2-N1-C1-S1 = -0.9(2)°, ∠C3-S1-C1-N1 =0 .4(1)°, ∠C1-N1-C2-C3 =1 .1(2)°, ∠N1-C2-C3-S1 = -0.8(2)°and ∠C1-S1-C3-C2 =0.3(1)°.In addition the torsion angles ∠C19-C3-C2-C13 = -3.7(3)°, ∠C12-N1-C2-C13 =9 .8(2)°and ∠C4-N2-C1-S1 = -1.5(2)°s how that thiazole rings are coplanar with C19, C13, C12, N2 and C4, and, because of steric hindrances, the phenyl group attached to C2 is not coplanar with thiazole ring.…”

mentioning

confidence: 88%

Crystal structure of 3,5-dimethyl-4-phenyl-2-phenylethylimino-3Hthiazole hydrobromide monohydrate, C19H21BrN2S · H2O

Samimi¹,

Mamaghani²,

Tabatabaeian³

2010

Zeitschrift Für Kristallographie - New Crystal Structures

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C 19 H 23 BrN 2 OS, monoclinic, P2 1 /n (no. 14), a =9.6170(6) Å, b =9.0048(6) Å, c =21.494(1) Å, b =97.817(1)°, V =1844.1 Å 3 , Z =4,Rgt(F) =0.030, wR ref (F 2 ) =0.069, T =100 K. Source of materialTo asolution of 2-phenylethanamine (0.12 g, 1mmol) in EtOH (10 mL), methyl isothiocyanate (0.07 g, 1mmol) was added and the reaction mixture was stirred at 25°Cfor 3h.Then 2-bromo-1-phenylpropan-1-one (1 mmol) was added and the reaction mixture stirred further for 6h .T he mixture was concentrated with evaporation of the solvent under reduced pressure. Addition of water (4 mL) gave 3,5-dimethyl-4-phenyl-2-phenylethylimino-3H-thiazole hydrobromide monohydrate (0.38 g, 0.95 mmol) as a colorless solid in 95 %yield, mp. 140 -142°C. Elemental analysis -found: C, 56.11 %; H, 5.72 %; N, 6.78 %. calculated for C 19H23BrN2OS: C, 56.02 %; H, 5.69 %; N, 6.88 %. Experimental detailsAll hydrogen atoms were refined in isotropic approximatiom in riding model with the U iso (H) =1.2 U eq (C). The packing in the title crystal structure can be described as asuccession of parallel layers. These layers are interconnected through hydrogen bonding to at hree-dimensional network. In such alayer, the bromide anions, act as atriple acceptor, connects the organic layers to form network via connecting with free water molecules (figure, bottom). There are two kinds of hydrogen bonds N-H···Br and Br···H-O-H( figure, top). The bond dis- (2) Å are in the range reported in the literature [14][15][16][17]. The thiazole ring is planer as indicated with torsion angles ∠C2-N1-C1-S1 = -0.9(2)°, ∠C3-S1-C1-N1 =0 .4(1)°, ∠C1-N1-C2-C3 =1 .1(2)°, ∠N1-C2-C3-S1 = -0.8(2)°and ∠C1-S1-C3-C2 =0.3(1)°.In addition the torsion angles ∠C19-C3-C2-C13 = -3.7(3)°, ∠C12-N1-C2-C13 =9 .8(2)°and ∠C4-N2-C1-S1 = -1.5(2)°s how that thiazole rings are coplanar with C19, C13, C12, N2 and C4, and, because of steric hindrances, the phenyl group attached to C2 is not coplanar with thiazole ring. The bond length of d(N2-C1) =1.323(2) Å and angles of ∠N2-C1-S1 =120.9(1)°, ∠N2-C1-N1 =1 24.7(1)°, ∠C4-N2-C1 =1 20.9(1)°and ∠C1-N2-H=123.0°confirm the features of typical imine bond. The imine nitrogen N2 atom is bonded to Ha tom with d(N2-H2A) =0.901 Å.Methyl and epso carbon of phenyl group are in plane with the thiazole ring. The phenyl group attached to C5 and N2-C1 was connected by the ethyl group (C5-C6) in anticonformation. In addition there are two lattice water molecules and two Br in any unit cell which are linked through as quare framework. Discussion

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“…1-Aroyl-3-arylthioureas have been used in the synthesis of 1-aroyl-3-aryl-4-substituted imidazole-2-thiones [1], 2-(aroylimino)-3-aryl-4-methyl-1,3-thiazoline [2], benzothiazolyl-4-quinazolinones [3], pyrimidine-2-thiones [4], and 2-iminobenzthiozolotriazin-4-ones [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial activity of some new 1-aroyl-3-(substituted-2-benzothiazolyl)thioureas

et al. 2008

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Synthesis, crystal structure of some new 2‐(4‐methylbenzoylimino)‐3‐aryl‐4‐methyl‐1,3‐thiazolines

Cited by 23 publications

References 22 publications

Crystal structure of (2Z,5Z)-3-allyl-5-(4-(methylthio)benzylidene)- 2-(p-tolylimino)thiazolidin-4-one, C21H20N2OS2

Crystal structure of (2Z,5Z)-3-allyl-5-(4-(methylthio)benzylidene)- 2-(p-tolylimino)thiazolidin-4-one, C21H20N2OS2

Crystal structure of 3,5-dimethyl-4-phenyl-2-phenylethylimino-3Hthiazole hydrobromide monohydrate, C19H21BrN2S · H2O

Synthesis and antibacterial activity of some new 1-aroyl-3-(substituted-2-benzothiazolyl)thioureas

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