5-phenyl-lH-tetrazole

Am ino-l-phenyl-a-tetrazole, 5- Ami no-1-phenyl-lH-tetrazole or l-Phenyl-S-amino-tetrazole [Called in Beil 1-Phenyl-tetrazolon-(5)-imin], H2N C-N(C6H5 )- N. Scales(from... 

Refs l)Beil 26,(113) [216] 2)R.Stolle F,Helwerth,Ber 47,1140(1914) 3)R-Stoll et al,Ber 55,1294-5 1302(1922) 4)F.R. Benson.ChemRevs 41.16(1947) 5)Ph.Rochlin, D.B.Murphy S.Helf.JACS 76,1453(1954) 5-Amino-l-phenyl-a-tetrazole, 5-Amino 1-phenyl-lH-tetrazole or l-Phenyl-5-amino-tetrazole[Called in Beil 1-Phenyl-tetrazolon-(5>imin],H,N-C-N(C6H, )-N. Scales(from... 

Anilino-afor lH)-tetrazole or 5-Phenyl-amino-tetrazole, called in Beil Tetrazolon-(5)-anil, CgH5.HN.C-NH-N,... 

Chloro-l-phenyl-lH-tetrazole Phenyl tetrazole ether Palladium on carbon... 

A mixture of 3.44 g (9.63 mmoles) of 4-(2-di-n-propylaminoethyl)-7-hydroxy-2(3H)-indolone hydrobromide (U. S. Pat. No. 4,314,944), 22 cc of dimethylformamide, 1.79 g (9.91 mmoles) of 5-chloro-l-phenyl-lH-tetrazole, 220 cc of acetone, 10 cc of water and 2.90 g (21 mmoles) of anhydrous potassium carbonate was refluxed for about 3 hours at which time thin layer chromatographic analysis (silica gel GF, 75-23-2 ethyl acetate-methanol-conc. ammonium hydroxide) indicated that the reaction was complete. 

After cooling the reaction mixture in an ice-bath, the inorganic salts were removed by filtration and washed with acetone. The combined filtrates were concentrated in vacuo. The residual syrup was diluted with saturated brine and extracted with three portions of diethyl ether. The gathered extracts were dried over anhydrous magnesium sulfate, clarified with charcoal and treated with ethereal hydrogen chloride until precipitation was complete. The solid was slurried in diethyl ether and decanted several times, filtered and air-dried to give 3.8 g (86%) of tan 4-(2-di-n-propylaminoethyl)-7-(l-phenyl-lH-tetrazol-5-yloxy)-2(3H)-indolone hydrochloride. Recrystallization from 200 cc of hot acetonitrile gave 2.6 g (59%) of microcrystalline product, m.p. 245°C. 

Deprotonation-silylation of 1-methyl-lH-tetrazole exhibits predominant C-silylation at the 5-position to form l-methyl-5-trimethylsilyl-lH-tetrazole (it is not a SMA, silylated carbon atom being sp2). When this position is blocked by a silyl or a phenyl group, silylation occurs on the /V-methyl to yield SMA derivatives.158... 

In the reaction of N-arenesulfonyl-N -phenylcarbodiimides with HN3, the initial linear adducts 38 rearrange to give 5-arenesulfonylamino-l-phenyl-lH-tetrazoles 39. ... 

In 1998 Kocienski et al. [10] reported the results of systematic studies on the reaction of selected heterocychc sulfones with carbonyl compoimds. The best results were obtained using l-phenyl-lH-tetrazol-5-yl (PT) sulfones. hi the first series of experiments, the representative PT sulfone 241 (Scheme 74) was compared with its benzothiazolyl (BT) counterpart. The comparison was... 

Benzimidazol-Bildung wird auch bei der Photolyse von 5-Phenoxy-l-phenyl-lH-tetrazol beobachtet1 ... 

Phenprobamate 655 l-Phenyl-5-mercapto-lH-tetrazole 3666 Picramic acid 304... 

In 1998, Kociensky et al. proposed a variation of this method that obviated the use of Barbier-type conditions and made this sequence more compatible with complex aldehydic substrates [137]. They also extended the range of sulfone heterocycles to l-isoquinohnoyl, l-methyl-2-imidazoyl, 4-methyl-2-imidazoyl, 4-methyl-l,2,4-triazol-3-yl, and l-phenyl-lH-tetrazol-5-yl (hereafter denoted PT), with the latter system being the most promising. Among the various trends that they observed from 96 comparative experiments, it was deduced that the -alkyl PT-sulfones gave better yields than their BT-substituted counterparts (suggesting that PT sulfones are less prone to self-condensation). Moreover, careful combination of the solvent and the counter ion proved to have a profound effect on the yield and the stereochemical outcome of the elimination. 

Blakemore, P. R. Cole, W. J. Kocienski, P. J. Motley, A. A Stereoselective Synthesis of trawj -l,2-Disnbstituted Alkenes Based on the Condensation of Aldehydes with Metalated l-Phenyl-lH-tetrazol-5-yl Snlfones Synlett 1998, 26-28. Blakemore, P. R. The Modified Jnlia Olefination Alkene Synthesis via the Condensation of Metallated Heteroarylalkylsnlfones with Carbonyl Compounds /. Chem. Soc., Perkin Trans. 1 2002, 2563-2585. 

The scope of the heteronucleophiles added to nitroalkenes was also extended to different nitrogen derivatives. In this direction, Wang and coworkers [43] explored the addition of N-heterocycles, such as benzotriazole 37, lH-[l,2,3]triazole 38, and 5-phenyl-IH-tetrazole 39, to various nitroolefins bearing an aryl or alkyl side-chain (Scheme 34.12). The cinchona alkaloid derivative 40, bearing a phenolic-OH, was the most efficient in promoting this addition. 

In a recent paper by Salimbeni et al. [2], a novel series of such All antagonists has been presented on the basis of a comparative analysis of theoretical distributions of the electrostatic potential (inactive compounds and overlay studies, employing a computational model of an All active conformation, it was found that the compound named LR-B/081 [3, 4] (C3oH30N603S), i.e. 2-[(6-butyl-2-methyl-4-oxo-5- 4-[2-(lH-tetrazol-5-yl)phenyl] benzyl -3H-pyrimidin-3-yl)methyl]-3-thiophenecarboxylate (Scheme 1), was one of the most potent in the series, and was selected as a candidate for further studies. 

Nitrosamino-1-phenyl-a tetrazole or 5-Nitrosamino-1-pheny -lH-tetraxole [Called Jn Beil 1-PhenyI-tetrazol-diazonium-hydroxyd-(5)], (ON)HN.C-N(C6H5)-N, mw 190.17, N... 

Amino-1(p-nitrophenyl)-a-tetrazole, 5-Amino-l-(4-nitrophenyl)-lH-tetrazole or 1-(p-Nitro-phenyl)-5-aminotetrazole, H2N-C-N(C6H4 N02 )-N. 

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