Abstract
[reaction: see text] The solid-phase synthesis of 2,4-diaminoquinazolines is presented. The chemistry involves the sequential condensation of 2-aminobenzonitriles and amines starting from an acyl isothiocyanate resin via a traceless cleavage and cyclization. The alpha-1 antagonist prazosin was synthesized, as well as several other examples, in good yields and purity.
MeSH terms
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Adrenergic alpha-Antagonists / chemical synthesis*
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Adrenergic alpha-Antagonists / chemistry
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Amines / chemistry
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Cyclization
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Isothiocyanates / chemistry
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Nitriles / chemistry
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Prazosin / chemical synthesis*
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Prazosin / chemistry
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Quinazolines / chemical synthesis*
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Quinazolines / chemistry
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Resins, Plant / chemistry
Substances
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Adrenergic alpha-Antagonists
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Amines
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Isothiocyanates
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Nitriles
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Quinazolines
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Resins, Plant
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2,4-diaminoquinazoline
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isothiocyanic acid
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Prazosin