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The ‘ t ‐Amino Effect’ of ortho ‐Nitroso Amines. Synthesis of 2,6‐Diaminoadenine Derivatives from 6‐(Dialkylamino)‐5‐nitrosopyrimidines
Author(s) -
del Carmen Ruiz Ruiz Maria,
Vasella Andrea
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100098
Subject(s) - chemistry , nitroso , nitroso compounds , reactivity (psychology) , thermal decomposition , nitrosation , purine , medicinal chemistry , purine metabolism , organic chemistry , stereochemistry , enzyme , medicine , alternative medicine , pathology
The ‘ t ‐amino effect’ of amino‐nitroso compounds was documented by preparing the (dialkylamino)‐nitroso pyrimidines 4 – 18 , and cyclising them under thermal conditions in high yields to the purine derivatives 19 – 32 . The reactivity of the amino‐nitroso‐pyrimidines, particularly of 17 derived from diethyl iminodiacetate, and of 19 , derived from 1‐phenylimidazolidine, correlates with the stability of the intermediate azomethine ylide. Thermolysis of the amino‐nitroso‐pyrimidines 34 – 37 , possessing dialkylamino substituents at C(4) and C(6), proceeded by protiodenitrosation, leading to 38 – 41 .