Ring expansion of α-azidoazines: formation of the first examples of fully unsaturated monocyclic 1,3,5-triazepines

Photolysis of the 2-azidopyridines (3), 2-azidopyrazines (6), and 4-azidopyrimidines (8), having a strong electron-donating substituent, in the presence of methoxide ion or diethylamine results in ring expansion to give the corresponding fully unsaturated 1,3-diazepines (5) and 1,3,5-triazepines (7) and (9).

[1]  T. Tsuchiya,et al.  SYNTHESIS OF FULLY UNSATURATED MONOCYCLIC 1,2,5-TRIAZEPINES FROM 4-AZIDOPYRIDAZINES , 1988 .

[2]  T. Tsuchiya,et al.  Studies on Diazepines. XXVIII. Syntheses of 5H-1, 3-Diazepines and 2H-1, 4-Diazepines from 3-Azidopyridines , 1987 .

[3]  T. Tsuchiya,et al.  Studies on diazepines. XXVI. Syntheses of 6H-1,4-diazepines and 1-acyl-1H-1,4-diazepines from 4-pyridyl azides. , 1987 .

[4]  T. Tsuchiya,et al.  PHOTOLYSIS OF PYRIDYL AZIDES IN THE PRESENCE OF METHOXIDE IONS : FORMATION OF FULLY UNSATURATED 1, 3- AND 1, 4-DIAZEPINES , 1984 .

[5]  J. Nishiyama,et al.  Synthesis of some alkyl- and arylimidazoles , 1983 .

[6]  B. Christensen,et al.  A stereocontrolled synthesis of (+)-thienamycin , 1980 .

[7]  C. Wentrup,et al.  Isolation of diazacycloheptatetraenes from thermal nitrene-nitrene rearrangements , 1980 .

[8]  R. N. Butler Recent Advances in Tetrazole Chemistry , 1977 .

[9]  I. Saito,et al.  1,2,4-triazepines from the photochemical walk rearrangement of 3,4,7-triaza-2,4-norcaradienes , 1976 .

[10]  Masahīko Takahashi,et al.  The Reaction of 1,2,4,5-Tetrazines with 2-Phenyl-1-azirine. The Synthesis of 2H-1,2,4-Triazepine Derivatives , 1975 .

[11]  V. Nair Thermally induced skeletal rearrangement in a triazepine , 1975 .

[12]  A. Hassner,et al.  Cycloaddition of 1-azirines to 1,2,4,5-tetrazines. Synthesis and rearrangement of 1,2,4-triazepines , 1974 .

[13]  G. C. Johnson,et al.  Triazacycloheptatrienes: The cycloaddition of azirines to dicarbomethoxy-s-tetrazine , 1974 .

[14]  M. Tiŝler,et al.  Some Aspects of Azido-Tetrazolo Isomerization , 1973 .

[15]  J. Hyatt,et al.  Facile synthesis of 9H-pyrimido[4,5-b]indoles from photolysis of 8-phenyltetrazolo[1,5-c]pyrimidines in acidic media , 1972 .

[16]  C. Wentrup Hetarylnitrenes V. Reactions of Tetrazolopyrazine Ring Contraction of Nitrenodiazines in Solution. Preliminary communication , 1972 .

[17]  T. Tsuchiya,et al.  Photolysis of tetrazolo[1,5-b]pyridazines; formation of cyanocyclopropenes , 1972 .

[18]  Tadashi. Sasaki,et al.  Heteroaromaticity. XLIX. Tetrazolo-azido isomerization in heteroaromatics. I. Syntheses and reactivities of some tetrazolopolyazines , 1971 .

[19]  B. Stanovnik Photolysis of 6-azido-azolopyridazines , 1971 .

[20]  C. Wentrup,et al.  Hetarylnitrenes—I : Ring contraction and fragmentation in nitrenodiazines , 1970 .

[21]  C. Wentrup Hetarylnitrenes—II : Azido/tetrazoloazine tautomerisation, and evidence for nitrene formation in the gas-phase , 1970 .

[22]  C. Wentrup,et al.  Nitrogen scrambling in 2-pyridylnitrene , 1969 .

[23]  J. Montgomery,et al.  Reaction of some 4-chloro-5-nitropyrimidines with sodium azide. Oxadiazolo[3,4-d]pyrimidine 1-oxides , 1968 .

[24]  C. Wentrup,et al.  Reactions of excited molecules , 1968 .

[25]  J. Montgomery,et al.  STUDIES ON THE AZIDOAZOMETHINE-TETRAZOLE EQUILIBRIUM. I. 2-AZIDOPYRIMIDINES. , 1965, The Journal of organic chemistry.