One-pot synthesis and crystal structure of an unusual amidine derived from heterocyclic ketene aminal derivative

被引：2

作者：

Yang, Penghui ^{[1
]}

Wang, Wenzhen ^{[1
]}

Duan, Yanshan ^{[1
]}

Qu, Chengtun ^{[1
]}

Zhang, Qunzheng ^{[1
]}

机构：

[1] Xian Shiyou Univ, Coll Chem & Chem Engn, Xian 710065, Peoples R China

来源：

HETEROCYCLIC COMMUNICATIONS | 2013年 / 19卷 / 03期

关键词：

amidine; catalyst; crystal structure; heterocyclic ketene aminal (HKA); ketene aminals; synthesis;

D O I：

10.1515/hc-2012-0161

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

One-pot reaction of Meldrum's acid (1) and heterocyclic ketene aminal (HKA, 2) in acetone affords an unusual amidine HKA derivative 4. The reaction catalysts were optimized and it was found that L-proline is the best catalyst for the one-pot reaction. The mechanism is discussed. The structure of compound 4 was determined by single crystal X-ray analysis.

引用

页码：167 / 169

页数：3

共 12 条

[1]

Bruker, 2008, APEX2 SAINT SADABS

[2] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[3] Chemistry of Heterocyclic Ketene Aminals: Construction of Imidazo (pyrido)[1,2-a]pyridines and Imidazo(pyrido)[3,2,1-ij][1,8]naphthyridines via DABCO-Catalyzed Tandem Annulations [J].

Li, Ming ;

Zhou, Zhong-Min ;

Wen, Li-Rong ;

Qiu, Zhong-Xuan .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) :3054-3063

[4] A short history of SHELX [J].

Sheldrick, George M. .

ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2008, 64 :112-122

[5]

Wang MX, 2002, PROG NAT SCI, V12, P249

[6] Modulating the Reactivity of Heterocyclic Ketene Animals in MCR: Selective Construction of Tetrahydrobenzo[b]imidazo[3,2,1-ιj][1,8]naphthyridines [J].

Wen, Li-Rong ;

Liu, Chao ;

Li, Ming ;

Wang, Li-Juan .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (22) :7605-7614

[7] Reactions of Heterocyclic Ketene Aminals with 2-[3-Oxoisobenzofuran-1(3H)-ylidene]malononitrile: Synthesis of Novel Polyfunctionalized 1,4-Dihydropyridine-Fused 1,3-Diazaheterocycles [J].

Xu, Wen-Yuan ;

Jia, Yue-Mei ;

Yang, Jing-Kui ;

Huang, Zhi-Tang ;

Yu, Chu-Yi .

SYNLETT, 2010, (11) :1682-1684

[8] Reactions of Heterocyclic ketene aminals with baylis-hillman acetates: A novel synthesis of tetrahydropyridine-fused 1,3-diazaheterocycles [J].

Yaqub, Muhammad ;

Yu, Chu-Yi ;

Jia, Yue-Mei ;

Huang, Zhi-Tang .

SYNLETT, 2008, (09) :1357-1360

[9] 9-(4-Methoxybenzoyl)-1,2,3,4-tetrahydro-6H-pyrido[1,2-a]pyrimidin-6-one [J].

Yu, Chu-Yi ;

Yuan, Xue-Ning ;

Huang, Zhi-Tang .

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 :O3186-U3282

[10] A novel one-pot reaction of heterocyclic ketene aminals: Synthesis of a small library of tetrahydropyridinone-fused 1,3-diazaheterocycles [J].

Yu, Chu-Yi ;

Yang, Peng-Hui ;

Zhao, Mei-Xin ;

Huang, Zhi-Tang .

SYNLETT, 2006, (12) :1835-1840

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