New Efficient Synthesis of 6, 12-Dihydro-5H-quinazolino[3,2-a] quinazolin-5-ones via Ugi/Staudinger/Aza-Wittig/Addition/Nucleo-philic Acyl Substitution Sequence

被引：5

作者：

Yang, Mao-Lin ^{[1
]}

Chen, Hao-Ran ^{[1
]}

Zhao, Long ^{[1
]}

Ding, Ming-Wu ^{[1
]}

机构：

[1] Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2023年 / 55卷 / 03期

基金：

中国国家自然科学基金;

关键词：

quinazoline; 6,12-dihydro-5H-quinazolino[3,2-a]quinazolin-5-one; Ugi reaction; Staudinger reaction; aza-Wittig reaction; ONE-POT SYNTHESIS; ANTITUMOR EVALUATION; UGI; CONDENSATION; DERIVATIVES; EXPANSION;

D O I：

10.1055/a-1932-5811

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new efficient synthesis of 6, 12-dihydro-5H-quinazolino[3,2-a]quinazolin-5-ones by sequential Ugi/Staudinger/aza-Wittig/addition/nucleophilic acyl substitution has been developed. alpha-Amino amides, obtained from Ugi-3CR of 2-azidobenzaldehydes, methyl 2-aminobenzoates, and isocyanides in the presence of catalytic amount of phenylphosphinic acid, reacted with triphenylphosphine and isocyanates to give 6, 12-dihydro-5H-quinazolino[3,2-a]quinazolin-5-ones in good yields. This method provides a domino and effective strategy for the preparation of various substituted quinazolino[3,2-a]quinazolin-5-ones under mild reaction condition.

引用

页码：465 / 472

页数：8

共 11 条

[1] Stereoselective Synthesis of 12-Tetrazolyl Substituted (E)-5H-Quinazolino[3,2-a]quinazolines via Sequential Ugi-Azide/Staudinger/aza-Wittig/Addition/Ag(I)-Catalyzed Cyclization
Yang, Mao-Lin
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JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (03) : 1898 - 1906
[2] New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence
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[3] Synthesis of Luminescent Indolo[2,1-b]quinazolin-6(12H)-ones via a Sequential Ugi/Iodine-Promoted Cyclization/Staudinger/Aza-Wittig Reaction
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[5] A new approach to the pyrrolo[3,4-d] pyrimidine system via tandem Staudinger/aza-Wittig reaction of 5-acyl-4-azidomethyl-3,4-dihydropyrimidin-2(1H)-ones
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[6] New efficient synthesis of 1,2,4-triazolo[5,1-b]quinazolin-9(3H)-ones via a tandem aza-Wittig/heterocumulene-mediated annulation
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[7] New facile synthesis of imidazo[2,1-b]-1,3,4-thiadiazol-5(6H)-ones via aza-Wittig reaction
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SYNTHESIS-STUTTGART, 2004, (07): : 1067 - 1071
[8] Efficient Synthesis of 2-Substituted Quinolino[7′, 8′:5, 6]pyrano-[2, 3-d]pyrimidin-4(3H)-ones via Tandem Aza-Wittig Reaction
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[9] Efficient Synthesis of 7-benzyl-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno [2,3-d]pyrimidin-4(3H)-Ones Via Aza-Wittig Reaction
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[10] Efficient Synthesis of 2-Substituted Quinolino[7',8':5,6]pyrano-[2,3-d]pyrimidin-4(3H)-ones via Tandem Aza-Wittig Reaction
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