Crystal Structure of 2-Chloro-3-(β-nitrovinyl)quinoline

Palani, K.; Ambalavanan, P.; Ponnuswamy, M. N.; Yathirajan, H. S.; Prabhuswamy, B.; Raju, C.; Nagaraja, Padmarajaiah; Shashikanth, S.

doi:10.2116/analsci.20.403

Cited by 4 publications

(4 citation statements)

References 6 publications

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“…An ORTEP diagram [13] of molecule 3 with atom numbering scheme is shown in Figure 3. The bond distances and angles are consistent with the reported values for other chloroquinoline derivatives [14–18]. The 2‐chloroquinoline ring is essentially planar with a maximum deviation of 0.024(1) Å of C9 atom from the least‐squares plane through the remaining nonhydrogen atoms.…”

Section: Resultssupporting

confidence: 86%

Synthesis of novel quinoline analogues of nimesulide: An unusual observation

Reddy

Nakka

Alishetty

et al. 2011

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Reduction of nimesulide followed by treating the N-acyl derivative of resulting arylamine with Vilsmeier-Haack reagent provided novel 2-chloro-3-formylquinoline derivatives. The construction of quinoline ring using Vilsmeier-Haack reagent afforded an unexpected compound, N-(2-chloro-3-formyl-7phenoxy quinolin-6-yl)formamide, in addition to the expected product. The structure of this unexpected quinoline derivative was established via single-crystal X-ray analysis and its formation could be explained by an unprecedented N-S bond cleavage under Vilsmeier-Haack reaction conditions. The 2chloro-3-formylquinoline derivatives obtained were converted to a number of corresponding Schiff bases with potential pharmacological importance.

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Section: Resultssupporting

confidence: 86%

Synthesis of novel quinoline analogues of nimesulide: An unusual observation

Reddy

Nakka

Alishetty

et al. 2011

Journal of Heterocyclic Chem

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“…The C1=N1 and N1-C5 distances of 1.283(7) and 1.350(7) Å are deviated significantly from the standard distances. The carbon-chlorine [C1-Cl] distance of 1.734 (6) Å is comparable with the values as obtained in an analogous structure of 2-chloro-3-(ß-nitrovinyl)quinoline (Palani et al, 2004). The Br-C10 distance of 1.956(6) Å is quite close to the standard value of 1.94 Å (Schneider et al, 2008).…”

Section: Resultssupporting

confidence: 80%

“…Quinolines and their derivatives are important scaffolds because of their wide spectrum of biological activities (Saito et al, 2001;Lekhok et al, 2008). They are used as efficient drugs for the treatment of malaria (Robert et al, 1998;Palani et al, 2004) and possess antibacterial, antiarrhythmic, antihypertensive and antibiotic properties as well. Quinoline alkaloids also act as immuno-suppressant inhibitors and virucides (Gilchrist et al, 1997;Kouznetsov et al, 1998;Garcia et al, 2000).…”

Section: Introductionmentioning

confidence: 99%

X-ray structure and activity analysis of 3-bromomethyl -2-chloro-quinoline

Kant

Kohli

Chhajer

et al. 2010

JANS

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Abstract:The structure of 3-bromomethyl-2-chloro-quinoline crystallizes in the triclinic crystal space group P'1 with unit cell parameters a=6.587(2), b=7.278(3), c=10.442(3) Å, a= 83.59(3)°, b= 75.42(2)°, g= 77.39(3)°, Z= 2, V= 471.9(3)Å 3 . The structure has converged to a final R-value of 0.0734. The phenyl Ring-B has normal geometry while the pyridine Ring-A has slightly distorted conformation. The asymmetry parameter calculations, i.e., DC 2 and DC s for the pyridine ring indicates that the structure is planar. There exists one intramolecular hydrogen bonded interaction of the type C-H…Cl and one C-H…N intermolecular interaction. The structure is stabilized by Van der Waals forces.

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“…The remaining angles lie within narrow ranges in both structures. A search of the CSD for 2-chloroquinoline groups containing a C atom attached at position 3 revealed only the following structures: 2-chloro-3-(chloromethyl)quinoline (CSD refcode ATEDEI; Lu et al, 2003), 1,5-bis(4-chlorophenyl)-3-(2-chloroquinolin-3-yl)pentane-1,5-dione (MAZZET; Insuasty et al, 2006) Belfaitah et al, 2006) and 2-chloro-3-(-nitrovinyl)quinoline (QAMNAU; Palani et al, 2004).…”

Section: Commentmentioning

confidence: 99%

Novel chalcones derived from 2-chloro-3-formyl-6-methylquinoline

et al. 2008

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Molecules of (E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-iodo-2-thienyl)prop-2-en-1-one, C(17)H(11)ClINOS, (I), and (E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-methyl-2-furyl)prop-2-en-1-one, C(18)H(14)ClNO(2), (II), adopt conformations slightly twisted from coplanarity. Both structures are devoid of classical hydrogen bonds. However, nonclassical C-H...O/N interactions [with C...O = 3.146 (5) A and C...N = 3.487 (3) A] link the molecules into chains extended along the b axis in (I) and form dimers with an R(2)(2)(8) motif in (II). The structural analysis of these compounds provides an insight into the correlation between molecular structures and intermolecular interactions in compounds for drug development.

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Crystal Structure of 2-Chloro-3-(β-nitrovinyl)quinoline

Cited by 4 publications

References 6 publications

Synthesis of novel quinoline analogues of nimesulide: An unusual observation

Synthesis of novel quinoline analogues of nimesulide: An unusual observation

X-ray structure and activity analysis of 3-bromomethyl -2-chloro-quinoline

Novel chalcones derived from 2-chloro-3-formyl-6-methylquinoline

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