The ‘t‐Amino Effect’ of ortho‐Nitroso Amines. Synthesis of 2,6‐Diaminoadenine Derivatives from 6‐(Dialkylamino)‐5‐nitrosopyrimidines |
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Authors: | Maria del Carmen Ruiz Ruiz Andrea Vasella |
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Affiliation: | Laboratorium für Organische Chemie, ETH Zürich, Wolfgang‐Pauli‐Strasse 10, CH‐8093 Zürich |
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Abstract: | 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 . |
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Keywords: | ‘ t‐Amino effect’ Nitroso amines Adenine, 2,6‐diamino‐ Pyrimidines, 6‐(dialkylamino)‐5‐nitroso‐ Purines, 2,6‐diamino‐, tricyclic |
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