摘要:

AbstractThe synthesis of 7‐chloro‐4‐(4‐diethylamino‐1‐methylbutylamino)‐2‐methoxy‐1,5‐naphthyridine, a compound which incorporates the structure of both chloroquine (a schizontocidal drug) and pamaquine (a gametocytocidal drug), has been carried out. In addition, two structurally related derivatives, the, “5‐azachloroquine” and the “5‐azapamaquine,” have also been obtained by multi‐step syntheses. “5‐Azachloroquine” possesses good antimalarial activity againstPlasmodium berghei.The compound was also found to be less toxic than the known 4‐aminoquinolin

ISSN:0022-152X    

DOI:10.1002/jhet.5570070301

出版商:Wiley‐Blackwell    

年代:1970

数据来源: WILEY

摘要:

AbstractThe cyclic nitrones 7‐chloro‐1,3‐dihydro‐5‐phenyl‐2H‐1,4‐benzodiazepin‐2‐one 4‐oxide (5a) and 1,3‐dihydro‐7‐methylthio‐5‐phenyl‐2H‐1,4‐benzodiazepin‐2‐one 4‐oxide (5b) are photoisomerized to readily isolable oxaziridines, 7‐chloro‐4,5‐epoxy‐5‐phenyl‐1,3,4–5‐tetrahydro‐2H‐1,4‐benzodiazepin‐2‐one (6a) and 4,5‐epoxy‐5‐phenyl‐1,3,4,5‐tetrahydro‐7‐methylthio‐2H‐1,4‐benzo‐diazepin‐2‐one (6b). Oxaziridine6bupon further irradiation gave ring expansion and ring contraction products, 4,6‐dihydro‐2‐phenyl‐9‐methylthio‐5H‐1,3,6‐benzoxadiazocin‐5‐one (7b) and 4‐benzoyl‐3,4‐dihydro‐6‐methylthioquinoxalin‐2(1H)‐one (8b) respectively. The

ISSN:0022-152X    

DOI:10.1002/jhet.5570070302

出版商:Wiley‐Blackwell    

年代:1970

数据来源: WILEY

摘要:

AbstractAn infrared spectral investigation of 2– and 4‐pyridone hexachloroantimonates and hexachlorostannates is reported. Protonation of these pyridones occurs on oxygen to form the 2‐ and 4‐hydroxypyridinium ions, as witnessed by the presence of both OH and NH stretching bands. Aromatic ring and skeletal frequencies in these cations correlated very well with those found in other 2– and 4‐substituted pyridinium hexachloroantimonates included in

ISSN:0022-152X    

DOI:10.1002/jhet.5570070303

出版商:Wiley‐Blackwell    

年代:1970

数据来源: WILEY

摘要:

AbstractAn infrared spectral investigation of a number of pyrimidine and pyrimidone hexachloroantimonates is reported. Typical aromatic absorption bands found in pyrimidinium salts were absent in the pyrimidone cations. 2‐And 4‐Pyrimidone hexachloroantimonates, as well as theirN‐methyl‐ andN,N'‐dimethyl derivatives, exhibit intense carbonyl absorption bands between 1720–1729 cm−1(solid state) which corroboratesN‐protonation

ISSN:0022-152X    

DOI:10.1002/jhet.5570070304

出版商:Wiley‐Blackwell    

年代:1970

数据来源: WILEY

摘要:

AbstractThe total synthesis of (±)‐capaurine (1) confirmed the suggested structure of

ISSN:0022-152X    

DOI:10.1002/jhet.5570070305

出版商:Wiley‐Blackwell    

年代:1970

数据来源: WILEY

摘要:

Abstract4‐Dicyanomethylene‐4H‐pyrans react with secondary amines to give 2‐aminopyridine and 2‐pyridone derivatives which, in turn, have been used to prepare copyrine derivatives. These pyrans and primary amines gave copyrine and iminopyridone derivatives in addition to the dicyanomethylene‐1,4‐dihydropyridines, which had been reported previously. Reaction of cyanocarbamoylmethylene‐4H‐pyrans with secondary amines gave 2‐pyrones, and with primary amines, gave copyrines and 1,4‐dihydr

ISSN:0022-152X    

DOI:10.1002/jhet.5570070306

出版商:Wiley‐Blackwell    

年代:1970

数据来源: WILEY

摘要:

AbstractCyclization of one of two cyclic bisamides (III and IX), followed by reduction and successive methylation, gave our expected bis‐coclaurine derivatives, one of which was identical withO‐methyloxyacanthine, namely natural obaberine

ISSN:0022-152X    

DOI:10.1002/jhet.5570070307

出版商:Wiley‐Blackwell    

年代:1970

数据来源: WILEY

摘要:

AbstractAn investigation of hybrids of 2,5‐dimethyl‐1,3,4‐oxadiazole (I) and α,α,α,α',α',α'‐hexachloro‐p‐xylene (Hetol®) (II) as potential antimalarial agents led to the synthesis of representative 2‐phenyI‐5‐(trichloromethyl)‐1,3,4‐oxadiazoles (VIa‐f, VIII‐X) and related trichloromethyl 1,2,4‐oxadiazole, 1,3,4‐oxadiazoles, and 1,3,4‐thiadiazole (VII, XIII‐XV). Treatment of the appropriately substituted benzoic: acid hydrazides (IVa‐f) with trichloroacetic anhydride afforded the intermediate 1‐benzoyl‐2‐(triehloroacetyl)hydrazines (Va‐f) which were cyclized to the desired 5‐(chlorophenyl, tolyl, or α,α,α‐trifluorotolyl)‐2‐(trichloromethyl)‐1,3,4‐oxadiazoles (VIa‐f) (44–66%)in situutilizing phosphorous oxychloride. Chlorination of the 5‐tolyl‐2‐(trichloromethyl)‐1,3,4‐oxadiazoles (VId‐f) afforded 2‐(trichloromethyl)‐5‐(α,α,α‐trichloro‐m‐ andp‐tolyl)‐1,3,4‐oxadiazole (VIII and IX) and 2‐(α,α,α,α',α',α'‐hexachloro‐3,5‐xylyl)‐5‐(trichloromethyl)‐1,3,4‐oxadiazole (X) in 23–56% yield. Each of the 2‐phenyl‐5‐(trichloromethyl)‐1,3,4‐oxadiazoles (VIa‐f, VIII‐X) was active againstPlasmodium bergheiin mice when administered in single 160 or 640 mg./kg. subcutaneous doses or given orally by drug‐diet for 6 days at doses of 29–336 mg./kg./day. The 2‐(trichloromethyl)‐5‐(α,α,α‐trichlorotolyl)‐1,3,4‐oxadiazoles

ISSN:0022-152X    

DOI:10.1002/jhet.5570070308

出版商:Wiley‐Blackwell    

年代:1970

数据来源: WILEY

摘要:

Abstract2‐Arylamino‐4,6‐dichloro‐s‐triazine reacts with cyanuric chloride in the presence of alkali to yieldN,N‐bis(4,6‐dichloro‐s‐triazin‐2‐yl)‐arylamine. In like manner, 2‐substitutedo‐chloro‐,p‐chloro‐,o‐nitro‐ andp‐carbomethoxyphenylamino‐4,6‐dimethoxy‐s‐triazines react with cyanuric chloride to yield the corresponding 4,6‐dichloro‐s‐triazin‐2‐yl‐4′,6′‐dimethoxy‐s‐triazin‐2′‐ylaryl‐amine, while anilino‐,p‐toluidino,o‐ andp‐methoxyphenylamino ando‐carbomethoxyphenylamino derivatives did not.The reaction of cyanuric chloride with 2,4‐dichloro‐6‐ethylamino‐s‐triazine in the presence of alkali yields the condensation product of the ditriazinylamine type and the reaction of cyanuric chloride w

ISSN:0022-152X    

DOI:10.1002/jhet.5570070309

出版商:Wiley‐Blackwell    

年代:1970

数据来源: WILEY

摘要:

AbstractThe synthesis of dihydrocytosines4from 3‐aminopropionitriles1has been broadened and the dihydrocytosines themselves have now been successfully converted to cytosines9. Unsubstituted 3‐(H, alkyl or aryl) aminopropionitriles (1, X = H) convert with cyanate to 1‐(H, alkyl or aryl)‐1‐(2‐cyanoethyl)ureas (2, X = H), which in turn easily cyclize with anhydrous strong acid or base to 1‐(H, alkyl or aryl)‐5,6‐dihydrocytosines (4, X = H). The 1‐arylaminopropionitriles (1, X = H) which are poorly reactive with cyanic acid combine readily with benzoylureas to form 3‐benzoyl‐1‐(2‐cyanoethyl)‐1‐arylureas (3, X = H). These benzoylureas likewise cyclize with strong acid or base but with simultaneous elimination of the benzoyl moiety to yield the 1‐aryldihydrocytosines4(X = H). Amines have successfully been added to 2‐chloroacrylonitrile to yield 2‐chloro‐3‐(amino and substituted amino)propionitriles (1, X = Cl). These 2‐chloropropionitriles also could be converted with cyanate or benzoylisocyanate to ureas and benzoylureas, respectively (1‐(H or alkyl)‐1‐(2‐chloro‐2‐cyanoethyl)ureas (2, X = Cl) or 1‐(H or alkyl)‐1‐(2‐chloro‐2‐cyanoethyl)‐3‐benzoylureas (3, X = Cl). The chlorine substituted ureas were unstable especially to base and to heat but with anhydrous acid were cyclized in high yield to 1‐(H or alkyl)‐5‐chloro‐5,6‐dihydro‐cytosines (4, X = Cl). Direct chlorination of unsubstituted dihydrocytosines4(X = H) did not afford these same 5‐chlorodihydrocytosines4(X = Cl) under any conditions investigated. 1‐Ethyl‐5,6‐dihydrocytosine (4b) as the cation (hydrobromide) is converted directly in good yield to 1‐ethylcytosine hydrobromide (7) by bromine in nitrobenzene at 140‐160° in a concomitant bromination dehydrobromination reaction. 1‐(Alkyl or aryl)‐5,6‐dihydrocytosines (4, X = H) are halogenated at low temperature in the presence of base to form (N3orN4)halogenodihydrocytosines (8, R = H). TheN‐chlorodihydrocytosines8are stable. TheN‐bromo andN‐iodo compounds isomerize spontaneously to 5‐halogeno‐5,6‐dihydrocytosines (4, X = Br, I; R = H). The 5‐halogeno‐5,6‐dihydrocytosines4(X = Cl

ISSN:0022-152X    

DOI:10.1002/jhet.5570070310

出版商:Wiley‐Blackwell    

年代:1970

数据来源: WILEY