Matches in SemOpenAlex for { <https://semopenalex.org/work/W2951284689> ?p ?o ?g. }
Showing items 1 to 77 of
77
with 100 items per page.
- W2951284689 abstract "Diphenyl phosphorazidate (DPPA) was used as the azide source in a one-pot synthesis of 2,2-disubstituted 3-amino-2H-azirines 1 (Scheme 1). The reaction with lithium enolates of amides of type 2, bearing two substituents at C(2), proceeded smoothly in THF at 0°; keteniminium azides C and azidoenamines D are likely intermediates. Under analogous reaction conditions, DPPA and amides of type 3 with only one substituent at C(2) gave 2-diazoamides 5 in fair-to-good yield (Scheme 2). The corresponding 2-diazo derivatives 6–8 were formed in low yield by treatment of the lithium enolates of N,N-dimethyl-2-phenylacetamide, methyl 2-phenylacetate, and benzyl phenyl ketone, respectively, with DPPA. Thermolysis of 2-diazo-N-methyl-N-phenylcarboxamides 5a and 5b yielded 3-substituted 1,3-dihydro-N-methyl-2H-indol-2-ones 9a and 9b, respectively (Scheme 3). The diazo compounds 5–8 reacted with 1,3-thiazole-5 (4H)-thiones 10 and thiobenzophenone (13) to give 6-oxa-1,9-dithia-3-azaspiro[4.4]nona-2,7-dienes 11 (Scheme 4) and thiirane-2-carboxylic acid derivatives 14 (Scheme 5), respectively. In analogy to previously described reactions, a mechanism via 1,3-dipolar cycloaddition, leading to 2,5-dihydro-1,3,4-thiadiazoles, and elimination of N2 to give the ‘thiocarbonyl ylides’ of type H or K is proposed. These dipolar intermediates with a conjugated CO group then undergo either a 1,5-dipolar electrocyclization to give spirohetrocycles 11 or a 1,3-dipolar electrocyclization to thiiranes 14." @default.
- W2951284689 created "2019-06-27" @default.
- W2951284689 creator A5023684409 @default.
- W2951284689 creator A5042377073 @default.
- W2951284689 creator A5078074518 @default.
- W2951284689 creator A5089102897 @default.
- W2951284689 date "2010-08-12" @default.
- W2951284689 modified "2023-09-27" @default.
- W2951284689 title "ChemInform Abstract: Diazo-Transfer Reaction with Diphenyl Phosphorazidate." @default.
- W2951284689 cites W2057805905 @default.
- W2951284689 doi "https://doi.org/10.1002/chin.199612048" @default.
- W2951284689 hasPublicationYear "2010" @default.
- W2951284689 type Work @default.
- W2951284689 sameAs 2951284689 @default.
- W2951284689 citedByCount "0" @default.
- W2951284689 crossrefType "journal-article" @default.
- W2951284689 hasAuthorship W2951284689A5023684409 @default.
- W2951284689 hasAuthorship W2951284689A5042377073 @default.
- W2951284689 hasAuthorship W2951284689A5078074518 @default.
- W2951284689 hasAuthorship W2951284689A5089102897 @default.
- W2951284689 hasConcept C134121241 @default.
- W2951284689 hasConcept C155647269 @default.
- W2951284689 hasConcept C161790260 @default.
- W2951284689 hasConcept C178790620 @default.
- W2951284689 hasConcept C185592680 @default.
- W2951284689 hasConcept C191897082 @default.
- W2951284689 hasConcept C192562407 @default.
- W2951284689 hasConcept C2776904781 @default.
- W2951284689 hasConcept C2778464347 @default.
- W2951284689 hasConcept C2778689049 @default.
- W2951284689 hasConcept C2779167645 @default.
- W2951284689 hasConcept C2779664164 @default.
- W2951284689 hasConcept C2780374730 @default.
- W2951284689 hasConcept C2780997848 @default.
- W2951284689 hasConcept C71240020 @default.
- W2951284689 hasConceptScore W2951284689C134121241 @default.
- W2951284689 hasConceptScore W2951284689C155647269 @default.
- W2951284689 hasConceptScore W2951284689C161790260 @default.
- W2951284689 hasConceptScore W2951284689C178790620 @default.
- W2951284689 hasConceptScore W2951284689C185592680 @default.
- W2951284689 hasConceptScore W2951284689C191897082 @default.
- W2951284689 hasConceptScore W2951284689C192562407 @default.
- W2951284689 hasConceptScore W2951284689C2776904781 @default.
- W2951284689 hasConceptScore W2951284689C2778464347 @default.
- W2951284689 hasConceptScore W2951284689C2778689049 @default.
- W2951284689 hasConceptScore W2951284689C2779167645 @default.
- W2951284689 hasConceptScore W2951284689C2779664164 @default.
- W2951284689 hasConceptScore W2951284689C2780374730 @default.
- W2951284689 hasConceptScore W2951284689C2780997848 @default.
- W2951284689 hasConceptScore W2951284689C71240020 @default.
- W2951284689 hasLocation W29512846891 @default.
- W2951284689 hasOpenAccess W2951284689 @default.
- W2951284689 hasPrimaryLocation W29512846891 @default.
- W2951284689 hasRelatedWork W1587534903 @default.
- W2951284689 hasRelatedWork W191066893 @default.
- W2951284689 hasRelatedWork W1967762855 @default.
- W2951284689 hasRelatedWork W1984501228 @default.
- W2951284689 hasRelatedWork W2014519432 @default.
- W2951284689 hasRelatedWork W2040924870 @default.
- W2951284689 hasRelatedWork W2049780965 @default.
- W2951284689 hasRelatedWork W2050123256 @default.
- W2951284689 hasRelatedWork W2050716691 @default.
- W2951284689 hasRelatedWork W2053269495 @default.
- W2951284689 hasRelatedWork W2057805905 @default.
- W2951284689 hasRelatedWork W2129310170 @default.
- W2951284689 hasRelatedWork W2774488512 @default.
- W2951284689 hasRelatedWork W2949670073 @default.
- W2951284689 hasRelatedWork W2950834311 @default.
- W2951284689 hasRelatedWork W2951049176 @default.
- W2951284689 hasRelatedWork W2951159665 @default.
- W2951284689 hasRelatedWork W2951594126 @default.
- W2951284689 hasRelatedWork W2952622690 @default.
- W2951284689 hasRelatedWork W3082449843 @default.
- W2951284689 isParatext "false" @default.
- W2951284689 isRetracted "false" @default.
- W2951284689 magId "2951284689" @default.
- W2951284689 workType "article" @default.