1993
DOI: 10.1021/jo00067a058
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Dialkyltin oxide mediated addition of trimethylsilyl azide to nitriles. A novel preparation of 5-substituted tetrazols

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Cited by 266 publications
(109 citation statements)
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“…[19][20][21] In addition, a new broad middle absorption around the 3400 cm −1 suggests the existence of water molecules in title compound. Crystallographic data of 1 (Table 1) suggest that title compound belong to monoclinc crystal system, C2/c space group.…”
Section: Resultsmentioning
confidence: 99%
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“…[19][20][21] In addition, a new broad middle absorption around the 3400 cm −1 suggests the existence of water molecules in title compound. Crystallographic data of 1 (Table 1) suggest that title compound belong to monoclinc crystal system, C2/c space group.…”
Section: Resultsmentioning
confidence: 99%
“…To the best of our knowledge, this type of Cu···Cu interaction is obviously stronger than that of tetrazole complex [Cu(Mtta)] n (3.484-3.592 Å) et al 20 and Cu I triazole coordination polymer (3.421 Å). 19 The attractive interactions between closed-shell d 10 metal centers have received extensive attention because they play an important role in optical and electronic properties of polynuclear d 10 metal complexes. 15,16,25 In addition, there exist a weak interaction uncoordinated water molecules and pyridyl group that are speculated to hold together the molecules of the compound.…”
Section: 24mentioning
confidence: 99%
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“…Thus, reaction of 13 with Bu 3 SnN 3 in 1,2-dimethoxyethane at reflux (DME, conditions b) followed by acidic workup 21 gave 17 100 in essentially quantitative yield. Another method, applying Me 3-SiN 3 and Bu 2 SnO (conditions c) for in situ generation of dibutyl trimethylsilyloxytin azide 22 was similarly efficient. Conditions a afforded tetrazoles 18 and 20 from the corresponding nitriles 14 and 16 in good and excellent yields, respectively; however, reaction of 15 to give the 1-naphthyl derivative 19 failed.…”
Section: Synthesesmentioning
confidence: 95%
“…8 It was later demonstrated that N-bromosuccinimide (NBS) 9 and 1,3-dibromo-5,5-dimethylhydantoin 10 can replace Br 2 in this reaction. 12 (E) The dehydrative condensation of 1,2-aminoalcohols with carbon dioxide (5 MPa) has been achieved in N-methylpyrrolidone (NMP) with Bu 2 SnO (10 mol%), and 2-oxazolidinones were obtained in 53-94% yield. These are useful intermediates for the synthesis of many target molecules, including polymers, agricultural chemicals, and biologically active compounds.…”
Section: Abstractsmentioning
confidence: 99%