Pyrolysis of Azido-diphenylpyrazines

Ohta, Akihiro; Watanabe, Tokuhiro; Nishiyama, Junko; Uehara, Kazue; Hirate, Rei

doi:10.3987/r-1980-12-1963

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Methods 3: Substitution By Acyl Groups1

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1981

2008

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Cited by 9 publications

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“…[422] 12.4.4.3.1.4 The usual reagents are acyl or aroyl halides or acid anhydrides in dry solvents, and the products are prone to nucleophilic attack (e.g., hydrolysis), which cleaves the group from the heterocyclic ring.…”

Section: Methods 3: Substitution By Acyl Groupsmentioning

confidence: 99%

Product Class 4: Benzimidazoles

Neier¹,

Bellus²

2002

Category 2, Hetarenes and Related Ring Systems

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Section: Methods 3: Substitution By Acyl Groupsmentioning

confidence: 99%

Product Class 4: Benzimidazoles

Neier¹,

Bellus²

2002

Category 2, Hetarenes and Related Ring Systems

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ChemInform Abstract: PYROLYSIS OF AZIDO‐DIPHENYLPYRAZINES

Ohta¹,

Watanabe²,

Nishiyama³

et al. 1981

Chemischer Informationsdienst

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Pteridines. Part CXIX.

Pfleiderer

2008

Helvetica Chimica Acta

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A variety of pyrimidine precursors 12–25 were converted into a series of new 7‐hydroxylumazines (=7‐hydroxypteridine‐2,4(1H,3H)‐diones) 26–35 which functioned as starting materials for the transformation into the corresponding 7‐chlorolumazines 36–45. Subsequent reaction with hydrazine led to the 7‐hydrazinolumazines 46–55 which gave on nitrosation the 7‐azidolumazines 1 and 56–64. These compounds were subjected to short heating in xylene whereby 1 and 56–61 showed a new pteridine–purine interconversion in forming a new type of 1,3‐disubstituted or 3‐substituted xanthin‐8‐amine‐derived nitrilium ylides (2,3,6,7‐tetrahydro‐N‐methylidyne‐2,6‐dioxo‐1H‐purin‐8‐aminium ylides) 11 and 65–70. The presence of an additional 6‐alkyl substituent in the 7‐azidolumazines 63 and 64 or of an unsubstituted N(3) position in 62 caused further rearrangement to xanthine‐9‐carbonitriles 71–73. Prolonged heating of 7‐azido‐1,3‐dimethyllumazine (1) also afforded theophylline‐9‐carbonitrile (=1,2,3,6‐tetrahydro‐1,3‐dimethyl‐2,6‐dioxo‐9H‐purine‐9‐carbonitrile; 5). The nitrilium ylide function was established by NMR and UV spectra as well as by elemental analyses. Confirmation of the nitrilium ylide structures was suggested by the result of the heating of 1,3‐dimethyl‐N‐methylidynexanthin‐8‐aminium ylide 11 in EtOH or of 1 in pentan‐1‐ol leading to 8‐aminotheophylline (=8‐amino‐3,7‐dihydro‐1,3‐dimethyl‐1H‐purin‐2,6‐dione; 74).

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Pyrolysis of Azido-diphenylpyrazines

Cited by 9 publications

References 0 publications

Product Class 4: Benzimidazoles

Product Class 4: Benzimidazoles

ChemInform Abstract: PYROLYSIS OF AZIDO‐DIPHENYLPYRAZINES

Pteridines. Part CXIX.

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