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Synthesis of novel 2-phenyl-5-substituted dihydropyrimidines using 2-phenyl-1,3-diaza-1,3-butadienes and electron-deficient olefins

Nishimura, Yoshio ; Yasui, Yoshizumi ; Kobayashi, Satoshi ; Yamaguchi, Masahiko ; Cho, Hidetsura

Tetrahedron, 2012-04, Vol.68 (16), p.3342-3350 [Peer Reviewed Journal]

Kidlington: Elsevier Ltd

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Title:
Synthesis of novel 2-phenyl-5-substituted dihydropyrimidines using 2-phenyl-1,3-diaza-1,3-butadienes and electron-deficient olefins
Author: Nishimura, Yoshio ; Yasui, Yoshizumi ; Kobayashi, Satoshi ; Yamaguchi, Masahiko ; Cho, Hidetsura
Subjects: 1,3-Diaza-1,3-butadiene ; 2,5-Disubstituted dihydropyrimidine ; Acrylonitriles ; Carbonyl compounds ; Chemistry ; Cyclization ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Olefins ; Organic chemistry ; Phenyls ; Preparations and properties ; Sulfones ; Synthesis (chemistry) ; Tautomerism ; Tautomers ; Tetrahedrons ; Tetrahydropyrimidine
Is Part Of: Tetrahedron, 2012-04, Vol.68 (16), p.3342-3350
Notes: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Description: A novel synthetic method for 2,5-disubstituted dihydropyrimidines was developed. The cyclization of 1,3-diaza-4-dimethylamino-1,3-butadienes having a N-protecting group (N-Boc, N-Cbz, N-n-C4H9, N-Bn or N-Ph) with electron-deficient olefins, such as α,β-unsaturated carbonyl compounds, phenyl vinyl sulfone, and acrylonitrile was studied in detail. The cyclization smoothly proceeded to afford 4-dimethylamino-1,4,5,6-tetrahydropyrimidines or 1,6-dihydropyrimidines in good yields. The isolated 4-dimethylamino-1,4,5,6-tetrahydropyrimidines were converted to 2,5-disubstituted-1,6-dihydropyrimidines through the β-elimination of the dimethylamino group. 2,5-Disubstituted-1,4(6)-dihydropyrimidines were obtained after removal of the N-Boc or N-Cbz group. Independent tautomers of the resulting dihydropyrimidines were observed. [Display omitted]
Publisher: Kidlington: Elsevier Ltd
Language: English

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Synthesis of novel 2-phenyl-5-substituted dihydropyrimidines using 2-phenyl-1,3-diaza-1,3-butadienes and electron-deficient olefins

Nishimura, Yoshio ; Yasui, Yoshizumi ; Kobayashi, Satoshi ; Yamaguchi, Masahiko ; Cho, Hidetsura

Kidlington: Elsevier Ltd

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