✦ LIBER ✦

Synthesis and [4+2] cycloaddition reactions of 4-(N-allyl-N-aryl)amino-1,3-diaza-1,3-butadienes with vinyl-, isopropenyl- and chloroketenes: Entry to novel pyrimidinone/fused pyrimidinone derivatives

✍ Scribed by Arun K Sharma; Mohinder P Mahajan

Book ID: 104208047
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 782 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00873-9

No coin nor oath required. For personal study only.

✦ Synopsis

4-(N-Allyl-N-aryl)amino-l,3-diaza-l,3-butadienes 2, prepared by the treatment of N-ary. lamino-l,3-diaza-l,3-butedienes 1 with allyi bromide, underwent [4+2] cycloadditions with vinyl/isol~of.,enyl-and accorapanied by rearrangements in case of chloroketenes, to yield 5-vinyl/isopmpenyl pyrimidinones 5 and 5-methylthio pyrimidinones 19, respectively. The pyrimidinones 5 on refluxing in xyiene gave pyrimidoazepines 6, underwent annelation reaction, in refluxing benzene in presence of AICI3, to yield pyrimidoquinolines 7 and on treatment with DMAD in refluxing toluene, underwent [4+2] eycloadditiun accompcnied by the elimination of N-allylarylamine functionality to yield q-uinazolinone 9. Further, the reactions of 5 with PhSH in the presence of AIBN in refluxing benzene followed unusual radical cyclisation involving N-aryl group leading to pyrimidequinolines 10. The iedocyclisatiun of l~Timidinones 19 yielded .l~rimidothiazines 20.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis and [4 +

ChemInform Abstract: Synthesis and [4 + 2] Cycloaddition Reactions of 4-(N-Allyl-N-aryl)amino-1,3-diaza-1,3-butadienes with Vinyl-, Isopropenyl- and Chloroketenes: Entry to Novel Pyrimidinone/Fused Pyrimidinone Derivatives.

✍ A. K. SHARMA; M. P. MAHAJAN 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 36 KB 👁 2 views

Regioselective [4+2] cycloaddition versu

Regioselective [4+2] cycloaddition versus nucleophilic reactions of N-arylamino substituted 1,3-diaza-1,3-butadienes with ketenes: Synthesis of pyrimidinone and fused pyrimidinone derivatives. Part II

✍ Paramita D Dey; Arun K Sharma; Prasad V Bharatam; Mohinder P Mahajan 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 564 KB

ChemInform Abstract: Regioselective [4 +

ChemInform Abstract: Regioselective [4 + 2] Cycloaddition versus Nucleophilic Reactions of N-Arylamino Substituted 1,3-Diaza-1,3-butadienes with Ketenes: Synthesis of Pyrimidinone and Fused Pyrimidinone Derivatives. Part 2.

✍ P. D. DEY; A. K. SHARMA; P. V. BHARATAM; M. P. MAHAJAN 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 37 KB 👁 2 views

Regioselective [4 + 2] Cycloaddition versus Nucleophilic Reactions of N-Arylamino Substituted 1,3-Diaza-1,3-butadienes with Ketenes: Synthesis of Pyrimidinone and Fused Pyrimidinone Derivatives. Part 2. -A novel synthetic method for substituted pyrimidinones (III) and (VIII) via reaction of the tit

Synthesis and regioselective [4+2] cyclo

Synthesis and regioselective [4+2] cycloaddition/nucleophilic reactions of N-arylamino-1:3-diaza-1:3-butadienes with ketenes and accompanying rearrangements

✍ Paramita D. Dey; Arun K. Sharma; Sachchida N. Rai; Mohinder P. Mahajan 📂 Article 📅 1995 🏛 Elsevier Science 🌐 French ⚖ 504 KB

A Novel Entry into 1-Methyl- and 1-Aryl-

A Novel Entry into 1-Methyl- and 1-Aryl-octahydropyrrolo[3,4-b]pyrroles and Their N-1—C-2 Fused Derivatives: Stereoselective Synthesis via an Intramolecular Azomethine Ylide Cycloaddition Reaction.

✍ Mahalingam Poornachandran; Raghavachary Raghunathan 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 16 KB 👁 2 views

ChemInform Abstract: A New Synthesis and

ChemInform Abstract: A New Synthesis and 1,3-Dipolar Cycloaddition of C-Aryl-N-(2,4-dibromophenyl)-nitrilimines with Arylmaleimides Leading to the Synthesis of 1-(2′,4′-Dibromophenyl)-3,5-diaryl-3a,4,6,6a-tetrahydro-1H,5H-pyrrolo [3,4-c]pyrazole-4,6-dione Derivatives.

✍ Kewal Krishan Singal; Baldev Singh; Balkar Singh 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB 👁 2 views

A New Synthesis and