SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF 2-SUBSTITUTED-2,3-DIHYDRO-5-THIOPHENOXY-1 H -1,3,2-BENZODIAZAPHOSPHOLE 2-OXIDES

Krishna

Journal of Chemical Research

et al. 2009

A series of some new class of 2-alkoxycarbonylamino-1,3,2-benzodiazaphosphole 2-oxides 4a-j were synthesised by reacting 3,4-diaminobenzophenone (3) with various dichlorophosphinyl carbamates (2) in dry toluene-tetrahydrofuran mixture (1:1) in the presence of triethylamine at 45-50°C. All the title compounds were evaluated for antimicrobial activity to determine their efficacy and were effective in suppressing the growth of bacteria and fungi. The chemical structures of the title products were characterised by IR, 1 H, 13 C and 31 P NMR and mass spectral studies.

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterisation and Antimicrobial Activity of Novel 2-alkoxycarbonylamino-1,3,2-benzodiazaphosphole 2-oxides

Krishna

Journal of Chemical Research

et al. 2009

“…However, it is observed that the exocyclic protons of the carboxamide group (NH-CO) of 4 and 5 resonated downfield (δ 10.69-10.89), when compared to others (δ 6.43-9.00). Endocyclic protons of N 1 and N 3 exhibited signals as doublets at δ  8.61-9.38 (J = 8.2-9.3 Hz) and 8.42-9.13 (J = 8.5-8.9 Hz) in all compounds 4-13, [26][27] due to their coupling with phosphorus. The chemical shifts of other protons of the carboxamide moiety appeared in the expected regions.…”

Section: Chartmentioning

confidence: 94%

Synthesis and antimicrobial activity of novel 2-(heteryl-carboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo[3,4-c] [1,3,2]diazaphosphole-2-oxides

Babu¹,

Kumar²,

Srinivasulu³

et al. 2007

Arkivoc

Some novel 2-(heterylcarboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo [3,4-c][1,3,2]diazaphosphole-2-oxides (4-13) have been synthesized from reaction of 3,4-diamino-1,2,5-oxadiazole (3) with various dichlorophosphinylcarboxamides (2), which were prepared by C-acylation of electron-rich heterocyclic compounds with dichloro isocyanato phosphine oxide (Kirsanov isocyanate) (1) in dry octane, in the presence of triethylamine at 50-60 °C. Their structures were determined by IR, 1 H, 13 C, 31 P NMR and mass spectral (MS) studies. They were screened for antifungal and antibacterial activity against Curvularia lunata / Aspergillus niger and Staphylococcus aureus / Escherichia coli, respectively. Most of these compounds exhibited moderate activity in the assays.

“…13 The most likely explanation is that the two signals arise from the protons on the two nitrogen atoms being in slightly different environments created by the ring substitution. The small difference in 31 P chemical shifts (40.64 vs 40.80 ppm) support this position.…”

Section: Methodsmentioning

confidence: 99%

“…2,10-Dichloro-6-[bis (2-chloroethyl)]amino -4,8-dinitrodibenzo[d,g] [1,3,6,2]-dioxathiaphosphocin 6-oxide (5), 2-bis(2-chloroethyl)amino-1,3, 2-dioxaphosphorinane 2-oxide (13), and 8-bis (2-chloroethyl)amino-6H-dinaphtho [2,1-d:1 ,2 ]1,3,2-dioxaphosphocin 8-oxide (15) were synthesized from a reaction of equimolar quantities of the corresponding precursor diols 3, 12, and 14 with coreagent N,N-bis(2-chloroethyl)-phosphoramidic dichloride (1) …”

Section: Synthesis and Spectral Studiesmentioning

confidence: 99%

Synthesis and Spectral Studies of 2,10-Dichloro-6-Bis(2-Chloroethyl)Amino-4,8-Dinitrodibenzo[ d , g ][1,3,6,2]-Dioxathiaphosphocin, 2,10-Dichloro-6-Bis(2-Chloroethyl)Amino-4,8-Dinitrodibenzo[ d , g ][1,3,6,2]Dioxathiaphosphocin 6-Oxide, 2-Bis(2-Chloroethyl)Amino-2,3-Dihydro-5-Thiophenoxy-1 H -1,3,2-Benzodiazaphosphole 2-Oxide, 2-Bis(2-Chloroethyl)Amino-1,2,3,4-Tetrahydro-1,3,2-Benzodiazaphosphorinane 2-Oxide, 5-Bromo-5-Nitro-2-Bis(2-Chloroethyl)Amino-1,3,2-Dioxaphosphorinane 2-Oxide, and 8-Bis(2-Chloroethy

Rao

Phosphorus, Sulfur, and Silicon and the Related Elements

et al. 2002

Self Cite

Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/gpss20 Synthesis and Spectral Studies of 2,10-Dichloro-6-Bis(2-Chloroethyl)Amino-4,8-Dinitrodibenzo[ d , g ] [1,3,6,2]-Dioxathiaphosphocin, 2,10-Dichloro-6-Bis(2-Chloroethyl)Amino-4,8-Dinitrodibenzo[ d , g ][1,3,6,2]Dioxathiaphosphocin 6-Oxide, 2-Bis(2-Chloroethyl)Amino-2,3-Dihydro-5-Thiophenoxy-1 H -1,3,2-Benzodiazaphosphole 2-Oxide, 2-Bis(2-Chloroethyl)Amino-1,2,3,4-Tetrahydro-1,3,2-Benzodiazaphosphorinane 2-Oxide, 5-Bromo-5-Nitro-2-Bis(2-Chloroethyl)Amino-1,3,2-Dioxaphosphorinane 2-Oxide, and 8-Bis(2-Chloroethyl)Amino-16 HDinaphtho[2,1-d :1′,2′-g ]1,3,2-Dioxaphosphocin 8-SYNTHESIS AND SPECTRAL STUDIES OF 2,10-DICHLORO-6-BIS(2-CHLOROETHYL)AMINO-4,8-DINITRODIBENZO[d,g][1,3,6,2]-DIOXATHIAPHOSPHOCIN, 2,10-DICHLORO-6-BIS(2-CHLOROETHYL)AMINO-4,8-DINITRODIBENZO[d,g][1,3,6,2]-DIOXATHIAPHOSPHOCIN 6-OXIDE, 2-BIS(2-CHLOROETHYL)AMINO-2,3-DIHYDRO-5-THIOPHENOXY-1H-1,3,2-BENZODIAZAPHOSPHOLE 2-OXIDE, 2-BIS(2-CHLOROETHYL)AMINO-1,2,3,4-TETRAHYDRO-1,3,2-BENZODIAZAPHOSPHORINANE 2-OXIDE, 5-BROMO-5-NITRO-2-BIS(2-CHLOROETHYL)AMINO-1,3,2-DIOXAPHOSPHORINANE 2-OXIDE, AND 8-BIS(2-CHLOROETHYL)AMINO-16H-DINAPHTHO-[2,1-d:1 ,2 -g]1,3,2-DIOXAPHOSPHOCIN 8-OXIDE-POTENTIAL ANTICANCER AGENTS