<i>N</i>‐Heteroaralkyl substituted α‐amidinium thiolsulfates

Parulkar, Anilkumar P.; Bauer, Ludwig

doi:10.1002/jhet.5570030417

Cited by 4 publications

(2 citation statements)

References 7 publications

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“…ZS, caled, 12.29; found, 11.78. /Ref aF, RNHC(=NH2+)CH2S203~+ H2S (ref 9 using the procedure for , -soluble Bunte salts); G, RNIIC(=NH2+)CH2C1C1 + (1) Na3SPQ3, (2) HC1, (3) 11202;H, RNI1C(=NH/)CH2S203: + S=C(NH2)2.…”

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2-Mercaptoacetamidine and derivatives as antiradiation agents

Westland¹,

Merz²,

Alexander³

et al. 1972

J. Med. Chem.

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A-Substituted-2-mercaptoacetamidines and functional derivatives, including the corresponding disulfides, Bunte salts, and phosphorothioates, have been synthesized and found as a class to be highly effective antiradiation agents. Variations in the N substituent include alkyl, cycloalkyl, cycloalkylalkyl, aralkyl, hydroxyalkyl, cycloalkyloxyalkyl, aryloxyalkyl, thioethers, and heteroaralkyl groups. A synthesis other than the conventional ones was needed and developed for the key intermediate, A-substituted-ethyl 2chloroacetimidate salt, in which the substituent possessed a bulky carbon skeleton. Treatment of 2chloroacetamides with Meerwein's reagent gave ethyl 2-chloroacetimidate fluoroborates (VI) (Ri or R2 = H) or (2-chloro-l-ethoxyethylidene)methylammonium tetrafluoroborates (VI) (Rj and R2 H). This allowed displacement of alkoxide by NH3 rather than by a bulky amine. Half-life determinations in EtOH were made of purified samples of VI in an attempt to correlate stability with successful preparation of 2-chloroacetamidine (V). Use of 1 -amino-2-propanol in the Pinner amidine synthesis resulted in a re-

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“…At least 90% survival rates in the ip test were observed with the cycloheptylmethyl (58), 1-adamantyl (59), 1 -adamantylmethyl (61), and 3-(l-adamantyl)propyl (62) derivatives of 2-mercaptoacetamidine (II). Radioprotection was obtained with ip doses as low at 2.5 mg/kg for 63, 3 mg/kg for 61, and 5 mg/kg for 62.…”

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confidence: 99%

2-Mercaptoacetamidine and derivatives as antiradiation agents

Westland¹,

Merz²,

Alexander³

et al. 1972

J. Med. Chem.

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Synthesis of 2‐amino‐4‐imino‐4,5‐dihydrothiazoles from N‐sulfonyl‐α‐chloroamidines and thiourea

Abdelaal

Bauer

1988

Journal of Heterocyclic Chem

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A number of new and interesting 2‐amino‐4‐(N‐substituted)imino‐4,5‐dihydrothiazoles were synthesized by reacting thiourea (or thiourea hydrochloride) with N‐alkyl‐ or N,N‐dialkyl‐N′‐p‐toluenesulfonyl‐α‐chloroacetamidines, where the N,N‐alkyl groups were ethyl, cyclohexyl, benzyl, β‐phenethyl, (3,5‐dimethyl‐1‐adamantyl)‐methyl, as well as N,N‐dimethyl‐ and N,N‐pentamethylene. Reactions of N‐alkyl‐N‐p‐toluenesulfonyl‐2‐chloroacetamidines (substituents being N‐ethyl, N‐benzyl and N,N‐dimethyl) with thiourea hydrochloride in hot 2‐propanol furnished 2‐amino‐4‐(p‐toluenesulfonyl)imino‐4,5‐dihydrothiazole (in 51, 60 and 65% yields, respectively) and the corresponding amine hydrochloride. In hot acetone or butanone, the reactions of these N‐sulfonyl‐2‐chloroacetamidines with excess thiourea provided 2‐amino‐4‐N‐(alkyl or N,N‐dialkyl)imminium‐4,5‐dihydrothiazole chlorides in 25–80% yield. The by‐product from these reactions was p‐toluenesulfonamide. The structures of the products were established by chemical transformations and spectral methods (nmr and mass spectra).

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