An efficient method to access 2‐triazolyl thio‐/selenopyridines with good to excellent yields by ruthenium(II)‐catalyzed one‐pot [3+2]/[2+2+2] cycloaddition reactions of azides, 1‐alkynyl thio‐/selenocyanates and 1,6‐diynes is reported. This atom‐economical catalytic strategy offers a mild and practical approach to access a variety of such cycloadducts with good to excellect regioselectivities. The protocol was further extended to the synthesis of 3,3′‐bis(triazolyl thio‐/seleno)‐2,2′‐bipyridines by the reaction of tetraynes with 1‐alkynyl thio‐/selenocyanates in the presence of aryl/alkyl azides.magnified image
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Several novel 2,4,8,10-tetra-t-butyl-6-substituted dibenzo [d , g] [1,3,6,2]dioxathiaphosphocin 6-oxides were synthesized in high yield by cyclocondensation of 2,2'-thiobis(2,4-di-t-butylphenol) with phosphorus oxychloride in the presence of triethylamine and a catalytic amount of dimethylaminopyridine (DMAP) in dry toluene followed by in situ reaction with different bulky phenols/thiophenols under the same reaction conditions. The structures of the synthesized compounds were confirmed by analytical, IR, multinuclear NMR studies. Their antibacterial and antifungal activities were evaluated against Staphylococcus aureus, Escherichia coli, Aspergillus niger and Fusarium oxysporium, respectively. Some of them showed moderate activity against these microorganisms.
RuII‐catalyzed intermolecular double [2+2+2] cycloadditions of 1,6‐diynes and alkynylthiocyanates have been developed for the synthesis of 2‐aryl thiopyridines. Aryl thiocyanates were isolated chemoselectively as a result of initial intermolecular [2+2+2] cycloaddition product. The method offers operational simplicity and is atom economical in nature.
In the title compound, C18H11Cl2O3PS, the seven‐membered phosphepine ring exhibits a distorted‐boat conformation, with the phosphoryl sulfide group axial and the dichlorophenoxy group equatorial. Fusion of the phosphepine ring to the biphenyl system causes strain, as evidenced by both widening and compression of the endocyclic angles in the heterocyclic ring. The P=S bond length is 1.8939 (12) Å and the planar dichlorophenyl ring is oriented at an angle of 28.70 (6)° to the phosphepine ring.
Several 6-trichloromethyl dibenzo[di] [1.3.2] dioxaphosphepin 6-oxide (3a), 2-chloroethoxy dibenzo[di] [1.3.2] dioxaphosphepin 6-oxide (3b) and alkylcarbamato dibenzo [di] [1.3.2] dioxaphosphepin 6-oxides (6a-c) have been synthesized from reactions of equimolar quantities of 2.2'-dihydroxybiphenyi (1) with trichloromethylphosphonic dichloride (2a), O-2-chloroethyi phosphoryldichloride (2b) and dichlorophosphinyl carbamates (5a-c) at 45-50°C for (3a & 3b) and 40-45°C for (6a-c) in dry toluene in the presence of tnethylamme. Elemental. IR and NMR (*H & "P) data have been discussed and supported all structures. Brought to you by | University of California Authenticated Download Date | 6/7/15 5:03 AM Vol. 7, No. 3, 2001 Synthesis and characterization of 6-substituted dibenzo[d,J][1,3,2Jdioxa phosphepin 6-oxides Brought to you by | University of California Authenticated Download Date | 6/7/15 5:03 AM Vol. 7, No. 3, 2001 Synthesis and characterization of 6-substituted dibenzo [dJ] [1,3,2]dioxa phosphepin 6-oxides solution of 1 (1.86 g, 0.01 mol) and triethylamine (2.02 g, 0.02 mol) in dry toluene (50 mL). When the addition was complete, the mixture was stirred and allowed to warm slowly to 40-45°C and maintained at this temperature for 7 hours. The completion of the reaction was monitored by TLC analysis. The solid triethylamine hydrochloride was filtered off and the solvent was evaporated under reduced pressure. The gummy residue was washed with water, dried and treated with 2-propanol. A white solid obtained after recrystallization of the crude product from 2-propanol afforded 6b, yield 0.192 g (60%), mp 250-252°C. Physical and spectral data of 6a-c are given in tables 1-2.
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