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Synthesis 1992; 1992(1/2): 106-112
DOI: 10.1055/s-1992-34176
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Reactivity of the Nitrogen-Silicon Bond. Pyridines and Furo[2,3-b][1,4]diazepines from 4-Amino-1-azabutadienes via 1,2-Dihydro-1,3,2-diazasilines

José Barluenga* , Miguel Tomás, Alfredo Ballesteros, Jian-She Kong
  • *Departamento de Química Organometálica, Facultad de Química, Universidad de Oviedo, E-33071-Oviedo, Spain
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Publication Date:
18 September 2002 (online)

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1,2-Dihydro-1,3,2-diazasilines 2 are prepared from 4-amino-1-azadienes 1 and react with dialkyl acetylenedicarboxylates to produce six- and seven-membered heterocycles depending on the substitution pattern of 1. Highly functionalized pyridine-2-carboxylates 5 and 8,8a-dihydro-2H-furo [2,3-b][1,4]diazepin-2-ones 11 are formed starting from azadienes 1 with R3 = H and R2 = R3 = H, respectively. On heating diazepines 11 undergo ring-contraction to alkyl 4-hydroxy-5-(iminomethyl) pyridine-2-carboxylates 13 which can be hydrolyzed to the corresponding 5-formyl-4-hydroxypyridine-2-carboxylates 14.