ChemInform Abstract: CONDENSATION OF PHENYLSULPHONYLACETIC ACID WITH ALDEHYDES

Naidu, M. S. R.; Reddy, D. Bhaskar

doi:10.1002/chin.197535163

Cited by 1 publication

(4 citation statements)

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“…13C nmr (CDClj) 21.7 (CH3), 124.3, 128.0, 129.0, 130.2, 132.1, 136.9, 138.7, 145.1 (all arom); eims miz (reí. int)303(M+, 10), 239 (M+-S02,4), 192(3), 178(3), 148(4), 139(Me-C6H4SO+, 100), 131 (3), 102 (7), 91 (19), 65 (10). All spectral data were identical with those of the natural product.…”

Section: Extractionmentioning

confidence: 61%

“…Synthesis of 1.-For confirmation, authentic 1 was synthesized essentially following literature procedures (10,11). [(4-Methylphenyl) sulfonyl] acetic acid (1.1 g), 4-nitrobenzaldehyde (0.75 g), and benzylamine (125 ml) were dissolved in HOAC (3.5 ml) and refluxed for 100 min.…”

Section: Extractionmentioning

confidence: 99%

“…Structure 1 was corrabo rated upon comparison with a synthetic sample, prepared from 4-nitrobenzaldehyde and [(4-methyl-phenyl) sulfonyl] acetic acid as per the modified Baliah method of synthesis of vinylic sulfones (10,11).…”

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confidence: 99%

“…C); eimsm/z(rel. int) 335 (M+, 2), 180(35), 179(33), 166{02NC6H4CH(0Me): 100], 150(10), 142 (9), 120(9), 91 (23). All spectral data were in agreement with those of the isolated pale yellow product.…”

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A New Aromatic Nitrosulfone from Cardiospermum corindum

Adinarayana¹,

Rao²,

Sarada³

1987

J. Nat. Prod.

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Dried leaves of Cardiospermum corindum yielded two, novel-type aromatic nitrosulfones [1,2]. The structures were established by spectroscopic analyses and synthesis.Compounds 1 and 2 were assigned the structures, 1-methyl-4-{ [2-(4-nitrophenyl) ethenyl } sulfonyl benzene and 1-{ [2-methoxy-2-(4-nitrophenyl) ethyl] sulfonyl } 4-methyl benzene, respectively.Morphologically, the climber Cardiospermum corindum L. (Sapindaceae) reflects spectacular adaptive diversities of development of yellow-tinged petals with supra basal scales presumably designed to favor cross pollination. The inflated fruit and worm-like seed with cordate hylum are advantageous for seed dispersal (1,2). Recently, this plant has attracted the attention of phytochemists (3-7). The present study is an attempt to discover new chemical compounds to match the relatively advanced morphology of the genus.Dried leaves of C. corindum collected near Tirupati, Chittoor District, Andhra Pradesh, India, were successively extracted with petrol, C6H6, and Me2CO. Five subsequent MeOH extracts each deposited a solid on cooling, which resulted in the isolation (see Experimental) of 3' ,4 '-di-0-methylluteolin-7^-D-gIucuronide (8), an orange compound [1], and, finally, a light yellow, crystalline product [2].The orange compound, according to eims, possessed the composition C15H13N04S. The compound had no optical activity. The ir spectrum displayed strong bands at 1340 and 1510 cm-1, as well as at 1140 and 1320 cm"1, indicative of the presence of -N02 and -S02 groupings, respectively. The 'H-nmr and 13C-nmr spectra suggested that the compound 1 was l-methyl-4-{ [2-(4 nitrophenyl) ethenyl} sulfonyl } benzene. This formulation was supported by the base peak fragment at m!z 139 (Me.C6H4.SO+) in the ms. On electron impact,/>-tolyl vinyl sulfones are known to undergo predominantly vinyl migration to oxygen with subsequent cleavage of the sulfur oxygen bond (9).

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Section: Extractionmentioning

confidence: 61%

Section: Extractionmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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