Total deprotection of N,N′-bis(tert-butoxycarbonyl)guanidines using SnCl4
摘要:
The total deprotection of N,N'-bis-Boc guanidines using SnCl4 proceeds smoothly in ethyl acetate at room temperature and leads to the easily isolable corresponding guanidinium chlorides. (C) 1997 Published by Elsevier Science Ltd.
2-Aminoquinazolines by Chan–Evans–Lam Coupling of Guanidines with (2-Formylphenyl)boronic Acids
作者:Aigars Jirgensons、Vitalii V. Solomin、Alberts Seins
DOI:10.1055/s-0040-1707080
日期:2020.9
A new method is presented for the synthesis of 2-aminoquinazolines, which is based on a Chan–Evans–Lam coupling of (2-formylphenyl)boronic acids with guanidines. Relatively mild conditions involving the use of inexpensive CuI as a catalyst and methanol as a solvent permit the application of the method to a wide range of substrates. Nonsubstituted, N-monosubstituted, and N,N-disubstituted guanidines
提出了一种合成 2-氨基喹唑啉的新方法,该方法基于(2-甲酰基苯基)硼酸与胍的 Chan-Evans-Lam 偶联。涉及使用廉价的 CuI 作为催化剂和甲醇作为溶剂的相对温和的条件允许该方法应用于广泛的基材。未取代的、N-单取代的和 N,N-二取代的胍可用作反应物,以从容易获得的(2-甲酰基苯基)硼酸以中等产率得到相应的 2-氨基喹唑啉。
Nucleophilic Substitution at the Guanidine Carbon Center via Guanidine Cyclic Diimide Activation
作者:Taeyang An、Yan Lee
DOI:10.1021/acs.orglett.1c03473
日期:2021.12.3
of the guanidine carbon centers, nucleophilic reactions at these sites have been underdeveloped because of the resonance stabilization of the guanidine group. We propose a guanidine C–N bond substitution strategy entailing the formation of guanidine cyclic diimide (GCDI) structures, which effectively destabilize the resonance structure of the guanidine group. In the presence of acid additives, the guanidine
GUANIDINE COMPOUNDS: IV. ACETYLATION OF SOME ALKYL-SUBSTITUTED GUANIDINES WITH ACETIC ANHYDRIDE AND ETHYL ACETATE
作者:R. Greenhalgh、R. A. B. Bannard
DOI:10.1139/v61-126
日期:1961.5.1
The acetylation of some mono-, N,N-, and N,N′-dialkylguanidines was studied using ethyl acetate and aceticanhydride. Except for the N,N-dialkylguanidines, the action of ethyl acetate on the free b...
Ultrasound-assisted synthesis of substituted guanidines using 1H-pyrazole-1-carboxamidine and S-methylisothiouronium sulfate under solvent-free conditions
作者:Mitsue Fujita、Yoshio Furusho
DOI:10.1016/j.tet.2018.06.057
日期:2018.8
We have investigated ultrasound-assisted synthesis of guanidine derivatives using 1H-Pyrazole-1-carboxamidine (PyzCA) and S-substituted isothiouronium sulfate (MeITU). The guanylations of several amines are promoted by ultrasound sonication under solvent-freeconditions, and proceed under mild conditions. It is of particular interest that the guanylations do not require bases in most cases.
THE REACTION OF ACETIC AND TRIFLUOROACETIC ANHYDRIDES WITH SOME SUBSTITUTED GUANIDINE HYDROCHLORIDES
作者:W. F. Cockburn、R. A. B. Bannard
DOI:10.1139/v57-171
日期:1957.11.1
Acetylation of the hydrochlorides of guanidine, cyclohexylguanidine, and 1-guanylpiperidine has been found to yield substituted triazines. Trifluoroacetylation of 1-guanylpiperidine hydrochloride also gives a triazine, whereas guanidine hydrochloride and cyclohexylguanidine hydrochloride are converted to bistrifluoroacetyl derivatives. The same triazines can also be obtained by acylation of the appropriate