1980
DOI: 10.1021/jo01295a033
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Novel rearrangement of a diaziridine

Abstract: Scheme II (a, 3 ), 3.20 (m, 2 ), 5.70 (m, 1 H), and 7.63 (m, 4 H).Preparation of 1,3-Diazacyclonona-1,2-diene (I). In scrupulously dried equipment under nitrogen,(5.00 g, 0.0169 mol), potassium tert-butoxide (MSA Research, 2.37 g, 0.0211 mol), and freshly distilled (from P206) methylene chloride (225 mL) were refluxed for 1 h. After the mixture was filtered, solvent was removed, and the resulting yellow liquid was distilled. I (1.54 g, 73.3%) was obtained [bp 48 °C (0.85 mm)]: IR (neat) 3000-2850, 2100 (s) c… Show more

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Cited by 5 publications
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“…1. Analysis of the ring bond lengths in (I) revealed that the phthalazine moiety exists in the expected more stable tautomeric form (Heine et al, 1980); C4---O2 1.253 (2), C4 N3 1.354 (2), N2--N3 1.381 (2), N2----C1 1.298 (2) and C1--O1 1.336 (2) ,~,. Other bond lengths and angles are in agreement with a central benzene ring and two appended carboxylate groups.…”
mentioning
confidence: 99%
“…1. Analysis of the ring bond lengths in (I) revealed that the phthalazine moiety exists in the expected more stable tautomeric form (Heine et al, 1980); C4---O2 1.253 (2), C4 N3 1.354 (2), N2--N3 1.381 (2), N2----C1 1.298 (2) and C1--O1 1.336 (2) ,~,. Other bond lengths and angles are in agreement with a central benzene ring and two appended carboxylate groups.…”
mentioning
confidence: 99%
“…From the 60s, various substituted diaziridines and diazirines were synthesized [29–43]. Halogen derivatives are ideal precursors for spectroscopic studies of carbens [44–46]; several derivatives were suggested as alkylating agents [47] and potential reagents for photolabeling of biological receptor sites [48–57], some of the substituted diaziridines and diazirines were investigated as anticancer drugs [58, 59], potential monoamine oxidase inhibitors [60, 61] and anesthetics [62, 63].…”
Section: Introductionmentioning
confidence: 99%