[2+2] Cycloaddition Reactions of Butadienyl Ketene with 1,4-Diazabuta-1,3-dienes: Synthesis of Functionalized Butadienyl-4-iminomethyl-azetidin-2-ones and Butenylidene-butadienyl-[2,2′-biazetidine]-4,4′-diones

被引：14

作者：

Bains, Deepak ^{[1
]}

Kumar, Yogesh ^{[1
]}

Singh, Prabhpreet ^{[2
]}

Bhargava, Gaurav ^{[1
]}

机构：

[1] Punjab Tech Univ, Dept Appl Sci, Kapurthala 144603, Punjab, India

[2] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2016年 / 53卷 / 05期

关键词：

DIELS-ALDER CYCLOADDITION; BETA-LACTAMS; ASYMMETRIC-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; 5-DIENYL PYRIMIDINONES; BUILDING-BLOCKS; RING EXPANSION; 1,3-DIAZABUTA-1,3-DIENES; TRANSFORMATION;

D O I：

10.1002/jhet.2465

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of butadienylketene with variety of 1,4-diazabuta-1,3-dienes are studied. The reactions resulted in the formation of previously unknown functionalized cis butadienyl-4-iminomethyl-azetidin-2-ones and butenylidene-butadienyl-[2,2'-biazetidine]-4,4'- diones. Butadienyl ketene reacts in [2+2] cycloaddition fashion with both iminic portion of 1,4-diazabuta-1,3-dienes and competitive [4+2] cycloaddition reaction of 1,4-diazabuta-1,3-dienes as 4 pi component with butadienyl ketene as 2 pi component are not observed.

引用

页码：1665 / 1669

页数：5

共 45 条

[1] Organocatalytic ring expansion of β-lactams to γ-lactams through a novel N1-C4 bond cleavage.: Direct svnthesis of enantiopure succinimide derivatives [J].

Alcaide, B ;

Almendros, P ;

Cabrero, G ;

Ruiz, MP .

ORGANIC LETTERS, 2005, 7 (18) :3981-3984

[2] Useful dual Diels-Alder Behavior of 2-azetidinone-tethered aryl imines as azadienophiles or azadienes:: A β-lactam-based stereocontrolled access to optically pure highly functionalized indolizidine systems [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM ;

Aly, MF .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) :3415-3426

[3] 4-Oxoazetidine-2-carbaldehydes as useful building blocks in stereocontrolled synthesis [J].

Alcaide, B ;

Almendros, P .

CHEMICAL SOCIETY REVIEWS, 2001, 30 (04) :226-240

[4] 1,3-Dipolar cycloaddition of 2-azetidinone-tethered azomethine ylides. Application to the rapid, stereocontrolled synthesis of optically pure highly functionalised pyrrolizidine systems [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM ;

Aly, MF .

CHEMICAL COMMUNICATIONS, 2000, (06) :485-486

[5] Direct organocatalytic synthesis of enantiopure succinimides from β-lactam aldehydes through ring expansion promoted by azolium salt precatalysts [J].

Alcaide, Benito ;

Almendros, Pedro ;

Cabrero, Gema ;

Ruiz, M. Pilar .

CHEMICAL COMMUNICATIONS, 2007, (45) :4788-4790

[6] β-lactams:: Versatile building blocks for the stereoselective synthesis of non-β-lactam products [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina .

CHEMICAL REVIEWS, 2007, 107 (11) :4437-4492

[7] Expeditious Entry to Enantiopure Mono- and Bis(Tricyclic) β-Lactams by Single or Double [2+2] Cycloaddition of Allenynes [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina ;

Gomez-Campillos, Gonzalo .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (02) :364-370

[8] A regio and diastereoselective transformation of 3-dienyl-2-azetidinones to novel pyrroloxazine [J].

Anand, Amit ;

Bhargava, Gaurav ;

Kumar, Vipan ;

Mahajan, Mohinder P. .

TETRAHEDRON LETTERS, 2010, 51 (17) :2312-2315

[9] Synthesis and biological activity of novel antibacterial quinazolines [J].

Bedi, PMS ;

Kumar, V ;

Mahajan, MP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (20) :5211-5213

[10] Highly diasteroselective and remarkably π-facially selective Lewis acid catalysed Diels-Alder cycloaddition reactions:: Access to novel 1,3,4-trisubstituted 2-azetidinones [J].

Bhargava, G ;

Mahajan, MP ;

Saito, T ;

Otani, T ;

Kurashima, M ;

Sakai, K .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (11) :2397-2405

← 1 2 3 4 5 →