2012
DOI: 10.3762/bjoc.8.69
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Chemistry of polyhalogenated nitrobutadienes, 10: Synthesis of highly functionalized heterocycles with a rigid 6-amino-3-azabicyclo[3.1.0]hexane moiety

Abstract: SummaryThe nitropolychlorobutadienes 3, 4 are valuable building blocks for various amination and successive heterocyclization products. Nucleophilic substitution reactions of the partially protected, bioactive amines 1, 2 with either vinyl, imidoyl or carbonyl chlorides result in the formation of the enamines 11, 12, 13, 16, 25, the amidine 6, and the amides 20, 21, respectively. In the following, cyclization to the highly functionalized pyrazoles 27, 28, pyrimidine 26 and pyridopyrimidine 24 succeeded. Deprot… Show more

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Cited by 21 publications
(17 citation statements)
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“…In the past ten years, different ways to synthesize persubstituted 4-nitropyrazoles have been developed [9,18,26,28,46]. Some of these compounds show high biological activities: they can…”
Section: Pyrazolesmentioning
confidence: 99%
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“…In the past ten years, different ways to synthesize persubstituted 4-nitropyrazoles have been developed [9,18,26,28,46]. Some of these compounds show high biological activities: they can…”
Section: Pyrazolesmentioning
confidence: 99%
“…Yield 0. (28). A solution of pyrimidine 27f (0.400 g, 1.2 mmol) and DDQ (0.600 g, 2.7 mmol) in toluene (10 mL) was heated to reflux for 5 h, allowed to cool down to r.t., and the precipitate filtered off.…”
Section: Synthesis Of [{1-mentioning
confidence: 99%
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“…[19][20][21][22] As additional neonicotinoid we used butadiene derivative 4 which had previously been synthesized by Zapol'skii et al starting from 2-chloro-5-(chloromethyl)pyridine 5 (Scheme 2). [23][24][25][26] For covalent attachment of neonicotinoids 1 and 4 to wood, implementation of a carboxylic acid function into the respective insecticides was to achieve. This was done by substitution reactions using suitable linking units 7-12 carrying an esterprotected carboxylic acid group.…”
Section: Synthesis Of the Neonicotinoidsmentioning
confidence: 99%
“…Polyhalo-1,3-butadienes, carrying at least one nitro group, are valuable starting materials for the directed synthesis of highly functionalized heterocycles with a wide variety of synthetically and/or physiologically interesting properties, [1][2][3][4] with 2-nitropentachloro-1,3-butadiene (1) being one of the most attractive members of this rather new class of synthetic building units. Starting from 1, the push-pull substituted thiophenes 3 are efficiently accessible in three steps via the aminodithiolanes 2 (Scheme 1).…”
Section: Introductionmentioning
confidence: 99%