- Synthesis of a novel ring-expanded purine analogue containing a 5:8-fused imidazo[4,5-e][1,2,4]triazocine ring system amidst opportunistic rearrangements and ring transformations
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A novel 5:8-fused heterocycle containing the imidazo[4,5-e][1,2,4]triazocine ring system has been synthesized in ten steps commencing from 1-benzyl-5-methyl-4-nitroimidazole. The compound is a new member of the family of ring-expanded xanthine-xanthosine analogues reported from this laboratory. The synthesis led to the unraveling of a number of novel rearrangements and ring-transformations.
- Burnett, Friedrick N,Hosmane, Ramachandra S
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p. 9567 - 9578
(2007/10/03)
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- Imidazo[4,5-e][1,2,4]Triazocine: A novel 5:8-fused ring system riddled with rearrangements
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Attempts to synthesize the title 5:8-fused heterocyclic ring system resulted in a number of novel opportunistic rearrangements and transformations. There is, however, some evidence to believe that one of these rearrangements might proceed through the transient intermediacy of this ring system.
- Burnett, Friedrick N.,Hosmane, Ramachandra S.
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p. 857 - 861
(2007/10/03)
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- Polycyclic guanine derivatives
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Novel polycylic guanine derivatives of the formula: STR1 wherein J is oxygen or sulfur, R1 is hydrogen, alkyl or alkyl substituted with aryl or hydroxy; R2 is hydrogen, aryl, heteroaryl, cycloalkyl, alkyl or alkyl substituted with ar
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- Synthetic approaches to 5:8-fused heterocyclic systems. A novel rearrangement during the synthesis of imidazo[4,5-e][1,2,4]triazocine ring system
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The attempted ring-closure of 4-amino-1-benzyl-5-[(N2-benzyl-N2- methoxycarbonyl)hydrazinomethylenecarbonyl]imidazole (5b) in sodium hydride/dimethyl sulfoxide at 50-60 °C afforded 1,7-dibenzylxanthine (6) instead of the anticipated 5:8-fused heterocycle 4b. A tentative reaction pathway has been proposed for the observed transformation.
- Burnett,Hosmane
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p. 325 - 328
(2007/10/02)
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