Alkylation of 4,5-dichloropyridazin-6-one with alpha,omega-dibromoalkanes 4,5-dichloro-1-(omega-bromoalkyl)pyridazin-6-ones

被引:15
作者
Kim, SK [1 ]
Cho, SD [1 ]
Kweon, DH [1 ]
Yoon, YJ [1 ]
Kim, JH [1 ]
Heo, JN [1 ]
机构
[1] AGROCHEM LABS,HANWHA GRP RES & ENGN CTR,TAEJON 305345,SOUTH KOREA
关键词
D O I
10.1002/jhet.5570340131
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkylations of 4,5-dichloropyridazin-6-one (1) with dibromoalkanes 2 or 3 in the presence of potassium carbonate or tetrabutylammonium bromide/potassium hydroxide were investigated under restricted condition. Reactions of 1 with 2 or 3, except for 2b and 3b, in the presence of potassium carbonate or tetrabutylammonium bromide/potassium hydroxide gave only the N-alkylation products 3 and/or 4. Alkylation of 1 with 2b or 3b in the presence of potassium carbonate yielded the N-alkylation products 3b and/or 4b and the O-alkylation product 5 as the main product, whereas treatment of 1 with 2b or 3b in the presence of tetrabutylammonium bromide/potassium hydroxide afforded selectively the N-alkylation products 3b and/or 4b.
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页码:209 / 214
页数:6
相关论文
共 10 条
[1]   SYNTHESIS OF NOVEL PYRIDAZINE ACYCLONUCLEOSIDES [J].
CHO, SD ;
CHUNG, JW ;
CHOI, WY ;
KIM, SK ;
YOON, YJ .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (05) :1199-1208
[2]   ALKYLATIONS OF HETEROCYCLIC AMBIDENT ANIONS .4. ALKYLATION OF 5-CARBETHOXY-2-PYRIDONE AND 5-NITRO-2-PYRIDONE SALTS [J].
CHUNG, NM ;
TIECKELM.H .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (08) :2517-&
[3]   N-ALKYLATION VS O-ALKYLATION IN THE MITSUNOBU REACTION OF 2-PYRIDONE [J].
COMINS, DL ;
GAO, JH .
TETRAHEDRON LETTERS, 1994, 35 (18) :2819-2822
[4]  
HOLAVA HM, 1971, J MED CHEM, V14, P262
[5]   Retro-ene reactions .3. Alkylation of 4,5-dichloro-1-hydroxymethylpyridazin-6-ones: Synthesis of 4,5-dichloro-1-(omega-phthalimido and saccharin-2'-ylalkyl)pyridazin-6-ones [J].
Kim, SK ;
Cho, SD ;
Moon, JK ;
Yoon, YJ .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (03) :615-618
[6]   THE PREPARATION OF SOME PYRIDAZONYL ACIDS [J].
KING, JA ;
MCMILLAN, FH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (13) :3222-3224
[7]   THE CHEMISTRY OF ALIPHATIC AND ALICYCLIC NITRO COMPOUNDS .9. THE MECHANISM OF THE REACTION OF SILVER NITRITE WITH ALKYL HALIDES - THE CONTRASTING REACTIONS OF SILVER AND ALKALI METAL SALTS WITH ALKYL HALIDES - THE ALKYLATION OF AMBIDENT ANIONS [J].
KORNBLUM, N ;
SMILEY, RA ;
BLACKWOOD, RK ;
IFFLAND, DC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (23) :6269-6280
[8]   MUCOCHLORIC ACID .2. REACTIONS OF THE ALDEHYDE GROUP [J].
MOWRY, DT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (08) :1909-1910
[9]  
NITTA Y, 1964, CHEM PHARM BULL, V12, P69
[10]  
YAMADA T, 1981, SYNTHESIS-STUTTGART, P631