1967
DOI: 10.1002/cber.19671000720
|View full text |Cite
|
Sign up to set email alerts
|

Über 1.2.4‐ Triazole, XIV. Die Bromierung von 1.2.4‐Triazolen

Abstract: Die Bromierung des 1.2.4-Triazols in alkalischer Losung fiihrt gleich zum 3.5-Dibrom-1.2.4triazol; 5-substituierte 1.2.4-Triazole ergeben unter gleichen Bedingungen die entsprechenden 3-Brom-1.2.4-triazole. Die Konstitution dieser Bromverbindungen wird durch Diazotierung der entsprechenden Aminoverbindungen in HBr sichergestellt. 3.5-Disubstituierte 1.2.4-Triazole liefern N-Brom-l.2.4-triazole, die sich durch sehr reaktionsfahiges Brom auszeichnen.Im 3-Brom-l.2.4-triazolon-(5), das bei der Spaltung des 3-Brom-… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

0
9
0

Year Published

1969
1969
2006
2006

Publication Types

Select...
6
1

Relationship

1
6

Authors

Journals

citations
Cited by 34 publications
(9 citation statements)
references
References 16 publications
0
9
0
Order By: Relevance
“…3,5-Dibromo-lH-I,2,4-triazole (10.0 g, 44.1 mntoles), prepared by the method of Kroger and Mietchen [23], was suspended in 200 ml of benz-vol. 23 ene, and 1.0 g (5 meq) of dihydropyran was added.…”
Section: Mar-apr 1986mentioning
confidence: 99%
“…3,5-Dibromo-lH-I,2,4-triazole (10.0 g, 44.1 mntoles), prepared by the method of Kroger and Mietchen [23], was suspended in 200 ml of benz-vol. 23 ene, and 1.0 g (5 meq) of dihydropyran was added.…”
Section: Mar-apr 1986mentioning
confidence: 99%
“…were obtained adapting conditions previously reported for the bromination of triazoles [7], while the coupling reaction involving complexes 3a and 3b was carried out using standard conditions similar to those reported for the coupling of heteroaromatic compounds. [8] NMR and HPLC analysis of 3a and 3b clearly indicate that only one isomer, N2 bound, is obtained in both cases.…”
Section: Resultsmentioning
confidence: 99%
“…The crude product was purified by column chromatography (toluene-EtOAc-EtOH, 15:1:1) to give 71 mg (60%) of 28 as a colorless syrup. 1 Deoxy-a-D-glucopyranosyl)-5-methoxy-1H-1,2,4-triazole (29) A mixture of diastereomers 19 and 26 (870 mg, 1.29 mmol) in EtOAc-MeOH (1:1, 30 mL) was treated with Pd/C in a hydrogen atmosphere as described for compound 28. Column chromatography (toluene-EtOAc-EtOH, 3:1:1; R f 0.19) gave 198 mg (59%) of 29 along with two incompletely deprotected by-products [R f 0.25 (20 mg) and R f 0.32 (70 mg)].…”
Section: -(2-deoxy-a-d-glucopyranosyl)-1h-124-triazole (28)mentioning
confidence: 99%
“…Column chromatography (toluene-EtOAc-EtOH, 3:1:1; R f 0.19) gave 198 mg (59%) of 29 along with two incompletely deprotected by-products [R f 0.25 (20 mg) and R f 0.32 (70 mg)]. 1 H NMR (250 MHz, CD 3 OD): d = 7.56 (s, 1 H, triazole-H), 5.91 (d, 1 H, 3 J 1,2 = 6.1 Hz, H-1), 4.56 (ddd, 1 H, 3 J 2a,3 = 5.5, 3 J 3,4 = 8.5, 3 J 2b,3 = 11.1 Hz, H-3), 4.09 (s, 3 H, OCH 3 ), 3.74 (dd, 1 H, 3 J 5,6a = 2.5, 2 J 6a,6b = 11.9 Hz, H-6a), 3.64 (dd, 1 H, 3 J 5,6b = 4.8, 2 J 6a,6b = 11.9 Hz, H-6b), 3.46 (ddd, 1 H, 3 J 5,6a = 2.5, 3 J 5,6b = 4.6, 3 J 4,5 = 9.6 Hz, H-5), 3.41-3.33 (m, 1 H, H-4), 2.40 (ddd, 1 H, 3 J 1,2a = 1.0, 3 J 2a,3 = 5.6, 2 J 2a,2b = 13.7 Hz, H-2a), 2.02 (ddd, 1 H, 3 J 1,2b = 6.2, 3 J 2b,3 = 11.1, 2 J 2a,2b = 13.7 Hz, H-2b). 13 C NMR (63 MHz, CD 3 OD): d = 161.1 (C-5 triazole), 148.1 (C-3 triazole), 80.0 (C-1), 76.6, 72.9, 70.0 (C-3, C-4, C-5), 62.6 (C-6), 59.1 (OCH 3 ), 36.4 (C-2).…”
Section: -(2-deoxy-a-d-glucopyranosyl)-1h-124-triazole (28)mentioning
confidence: 99%
See 1 more Smart Citation