Quinazolines. XIII. Synthesis of polycyclic 2,4-diaminopyrimidines from aromatic amine hydrochlorides and sodium dicyanamide

Rosowsky, A.; Papathanasopoulos, Nickolas

doi:10.1021/jo00936a033

Cited by 5 publications

(3 citation statements)

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“…An interesting reactivity involving dicyanamide was discovered in the early 1970s by Rosowsky et al [62]. Here, the authors observed an intramolecular aromatic electrophilic substitution under high-temperature conditions.…”

Section: Scheme 25mentioning

confidence: 90%

“…Later, this S E Ar reactivity was used for the synthesis of pyrroloquinazoline from 5-aminoindole [63]. Contrary to the one-pot procedure published by Rosowsky et al [62], these authors performed the reaction in two steps, by isolating the 5-indolylcyanoguanidine intermediate, in higher overall yields (Scheme 28). Interestingly, the addition of 5-aminoindole hydrochloride to the dicyanamide proceeded smoothly at 40 °C in DMF with a 90% yield.…”

Section: Scheme 25mentioning

confidence: 99%

“…Scheme 26:Examples for the synthesis of an 1,3-diaminobenzoquinazoline derivative by the S E Ar cyclization of arylcyanoguanidines[62].…”

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confidence: 99%

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Synthetic accesses to biguanide compounds

Grytsai

Ronco

Benhida

2021

Beilstein J. Org. Chem.

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Biguanide is a unique chemical function, which has attracted much attention a century ago and is showing resurgent interest in recent years after a long period of dormancy. This class of compounds has found broad applications such as reaction catalysts, organic strong bases, ligands for metal complexation, or versatile starting materials in organic synthesis for the preparation of nitrogen-containing heterocycles. Moreover, biguanides demonstrate a wide range of biological activities and some representatives are worldwide known such as metformin, the first-line treatment against type II diabetes, or chlorhexidine, the gold standard disinfectant and antiseptic. Although scarcely represented, the number of “success stories” with biguanide-containing compounds highlights their value and their unexploited potential as future drugs in various therapeutic fields or as efficient metal ligands. This review provides an extensive and critical overview of the synthetic accesses to biguanide compounds, as well as their comparative advantages and limitations. It also underlines the need of developing new synthetic methodologies to reach a wider variety of biguanides and to overcome the underrepresentation of these compounds.

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Section: Scheme 25mentioning

confidence: 90%

Section: Scheme 25mentioning

confidence: 99%