ICCAS OpenIR
The aza-ene reaction of heterocyclic ketene aminals with activated carbonyl compounds: a novel and efficient synthesis of gamma-lactam-fused diazaheterocycles
Zhang, JH; Wang, MX; Huang, ZT
1999-02-07
Source PublicationJOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN0300-922X
Issue3Pages:321-326
AbstractReactions of heterocyclic ketene aminals with activated carbonyl compounds are strongly influenced by the structure of the heterocycle moiety. Six-membered heterocyclic ketene aminals with or without an N-methyl group such as 3 and 4 underwent efficient addition and consecutive cyclocondensation reactions with diethyl oxomalonate 9 to produce gamma-lactam-fused pyrimidine derivatives 10 and 11 in moderate to excellent yield. For the five-membered enediamines, however, those compounds without any N-substituent such as 6 underwent the same reaction slowly and no reaction at all was observed with N-methyl and N,N'-dimethyl-substituted analogs 7 and 8. Heterocyclic ketene aminals 3 also reacted with glyoxylic acid esters 17 to afford 8-aroyl-7-hydroxy-6-oxo-1,2,3,4,6,7-hexa pyrrolo[1,2-a]pyrimidines 18 in good yield. No asymmetric induction-was found, however, when (1R,2S,5R)-(-)-menthyl glyoxylate 17b was employed as a chiral substrate. An aza-ene reaction mechanism involving heterocyclic ketene aminals as the aza-ene component (H-N-C=C) has been proposed. The effects of intramolecular hydrogen bonding and heterocyclic ring size on the reactivity are also discussed.
Indexed ByIC ; CCR ; SCI
Language英语
WOS IDWOS:000078696400015
PublisherROYAL SOC CHEMISTRY
Citation statistics
Cited Times:18[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/75112
Collection中国科学院化学研究所
Corresponding AuthorHuang, ZT
AffiliationChinese Acad Sci, Inst Chem, Beijing 100080, Peoples R China
Recommended Citation
GB/T 7714
Zhang, JH,Wang, MX,Huang, ZT. The aza-ene reaction of heterocyclic ketene aminals with activated carbonyl compounds: a novel and efficient synthesis of gamma-lactam-fused diazaheterocycles[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1,1999(3):321-326.
APA Zhang, JH,Wang, MX,&Huang, ZT.(1999).The aza-ene reaction of heterocyclic ketene aminals with activated carbonyl compounds: a novel and efficient synthesis of gamma-lactam-fused diazaheterocycles.JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1(3),321-326.
MLA Zhang, JH,et al."The aza-ene reaction of heterocyclic ketene aminals with activated carbonyl compounds: a novel and efficient synthesis of gamma-lactam-fused diazaheterocycles".JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 .3(1999):321-326.
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