Lewis Acid-Induced Hetero Diels-Alder Reaction of Conjugated Carbodiimides
作者： Takao Saito , Takahiro Ohkubo , Katsuhiro Maruyama , Hideki Kuboki , Shinichi Motoki
DOI: 10.1246/CL.1993.1127
关键词: Enamine 、 Diels–Alder reaction 、 Chemistry 、 Catalysis 、 Vinyl ether 、 Lewis acids and bases 、 Conjugated system 、 Aldehyde 、 Organic chemistry 、 Nitrogen 、 General chemistry
摘要: In the presence of a Lewis acid conjugated carbodiimides smoothly react as 2-azadienes with various dienophiles such acetylenic compound, enamine, vinyl ether, and aldehyde under mild reaction conditions to give good yields nitrogen heterocycles cycloadducts.
csj.jp参考文章(13)
Makoto Nitta, Hironobu Soeda, Shinya Koyama, Yukio Iino, On the Reaction of (Vinylimino)phosphoranes. Part 17. Preparation ofN-Vinylcarbodiimides and Their [4+2] Cycloaddition with Several Dienophiles to Give Pyridine Ring System Bulletin of the Chemical Society of Japan. ,vol. 64, pp. 1325- 1331 ,(1991) , 10.1246/BCSJ.64.1325
Pedro Molina, Antonio Arques, Maria Victoria Vinader, Jan Becher, Klaus Brondum, Fused pyrimidines by a tandem aza-Wittig/electrocyclic ring closure strategy: synthesis of pyrazolo[3,4-d]pyrimidine, [1,2,3]triazolo[4,5-d]pyrimidine, and thiazolo[4,5-d]pyrimidine derivatives Journal of Organic Chemistry. ,vol. 53, pp. 4654- 4663 ,(1988) , 10.1021/JO00255A003
Shoji EGUCHI, Takashi OKANO, Recent Advances in Synthetic Method of Nitrogen Heterocycles via Aza-Wittig Reaction Journal of Synthetic Organic Chemistry Japan. ,vol. 51, pp. 203- 211 ,(1993) , 10.5059/YUKIGOSEIKYOKAISHI.51.203
Takao Saito, Michio Nakane, Takashi Miyazaki, Shinichi Motoki, Conjugated heterocumulenes. Synthesis of CC- and NC-conjugated ketenimines through a Wittig-type reaction and their conversion into hetero(carbo)cycles Journal of The Chemical Society-perkin Transactions 1. pp. 2140- 2142 ,(1989) , 10.1039/P19890002140
Michihiko Noguchi, Kenjiro Onimura, Yuji Isomura, Shoji Kajigaeshi, Reaction of α,β-unsaturated carbodiimides with enamines leading to fused pyridine derivatives† Journal of Heterocyclic Chemistry. ,vol. 28, pp. 885- 890 ,(1991) , 10.1002/JHET.5570280409
Pedro Molina, Mateo Alajarín, Angel Vidal, One-pot preparation of rigid bicyclic guanidines from bis(iminophosphoranes) by a consecutive five-step process Journal of The Chemical Society, Chemical Communications. pp. 295- 296 ,(1992) , 10.1039/C39920000295
Pedro Molina, Antonio Arques, Pilar M. Fresneda, Maria Victoria Vinader, Maria De La Concepciòn Foces-Foces, Félix Hernandez Cano, Heterocyclization Reactions of Conjugated Heterocumulenes. Synthesis of Pyridine Derivatives by a Tandem Aza Wittig/Electrocyclization Strategy Chemische Berichte. ,vol. 122, pp. 307- 313 ,(1989) , 10.1002/CBER.19891220217
Jean-Charles Lancelot, Bertrand Letois, Carmela Saturnono, Paolo De Caprariis, Max Robba, A NOVEL SYNTHESIS OF 2,3-DIHYDRO[1,5]BENZOTHIAZEPIN-4(5H)-ONES Organic Preparations and Procedures International. ,vol. 24, pp. 204- 208 ,(1992) , 10.1080/00304949209355701
Takao Saito, Michio Nakane, Masanobu Endo, Hiromi Yamashita, Yoko Oyamada, Shinichi Motoki, CONJUGATED HETEROCUMULENES. SYNTHESIS OF C=C-CONJUGATED CARBODIIMIDES BY A WITTIG-TYPE REACTION OF IMINOPHOSPHORANES WITH ISOCYANATES AND THEIR CYCLOADDITIONS Chemistry Letters. ,vol. 15, pp. 135- 138 ,(1986) , 10.1246/CL.1986.135
Pedro Molina, Mateo Alajarin, Angel Vidal, J. Fenau-Dupont, J. P. Declerq, Domino Reactions - One-pot Preparation of Fluoreno[2,3,4-ij]isoquinoline Derivatives From Conjugated Ketene Imines Journal of Organic Chemistry. ,vol. 56, pp. 4008- 4016 ,(1991) , 10.1021/JO00012A039