Formal [3+2] cycloaddition reaction of [1,4]oxazin-2-ones and α-alkynyl ketones via a tandem Mukaiyama-Aldol addition/aza-cope rearrangement

被引：3
|
作者：
Obrecht, D [1 ]
Zumbrunn, C [1 ]
Müller, K [1 ]
机构：
[1] Hoffmann La Roche Ag, Pharma Res, CH-4070 Basel, Switzerland
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 18期
关键词：
D O I：
10.1021/jo9902695
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
引用
收藏
页码：6891 / 6895
页数：5
相关论文
共 21 条
  • [11] Exo/endo selectivity-control in Lewis-acid catalyzed tandem heterocyclization/formal [4+3] cycloaddition: synthesis of polyheterocycles from 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran
    Gao, Hongyin
    Wu, Xingxing
    Zhang, Junliang
    CHEMICAL COMMUNICATIONS, 2010, 46 (46) : 8764 - 8766
  • [12] In(OTf)3-catalyzed tandem aza-Piancatelli rearrangement/Michael reaction for the synthesis of 3,4-dihydro-2H-benzo[b][1,4]thiazine and oxazine derivatives
    Reddy, B. V. Subba
    Reddy, Y. Vikram
    Lakshumma, P. Subba
    Narasimhulu, G.
    Yadav, J. S.
    Sridhar, B.
    Reddy, P. Purushotham
    Kunwar, A. C.
    RSC ADVANCES, 2012, 2 (28): : 10661 - 10666
  • [13] Synthesis of Azepinoindoles via Rhodium -Catalyzed Formal Aza-[4+3] Cycloaddition Reaction of 3-Diazoindolin-2-imines with 1,3-Dienes in One-Pot
    Kim, Sanghyuck
    Kim, Hyunseok
    Um, Kyusik
    Lee, Phil Ho
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18): : 9808 - 9815
  • [14] An Efficient Approach to Original Substituted 2-Arylidene-2H-[1,4]-oxazin-3(4H)-ones via a Tandem Intramolecular P(O→C) Migration/Horner-Wadsworth-Emmons Olefination Sequence
    Claveau, Elise
    Gillaizeau, Isabelle
    Coudert, Gerard
    SYNLETT, 2009, (02) : 263 - 267
  • [15] SYNTHESIS OF 2,3,6,7-TETRAHYDRO-1H-1,4-DIAZEPINES AND 2,3,4,5,6,7-HEXAHYDRO-1H-1,4-DIAZEPINES VIA A TANDEM MICHAEL-TYPE ADDITION INTRAMOLECULAR AZA-WITTIG SEQUENCE
    BENALIL, A
    GUERIN, A
    CARBONI, B
    VAULTIER, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (09): : 1061 - 1064
  • [16] Metal-Free Intramolecular [3+2] Cycloaddition of γ-Hydroxy Acetylenic Ketones with Alkynes for the Synthesis of Naphtho[1,2-c]furan-5-ones and Its Derivatization via a Selective C(sp2)-H Deuteration Reaction
    Ning, Si-Si
    Meng, Dan
    Zhang, Jie-Yun
    Liu, Shi-Lei
    Zhou, Ni-Ni
    Jin, Xiaojie
    Zhu, Hai-Tao
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (11): : 7347 - 7358
  • [17] Highly Regio- and Diastereoselective Synthesis of 6,7-Dihydro-4H-furo[3,4-c]pyran Derivatives through Pd-Catalyzed Formal (3+3) Allylic Cycloaddition of 2-Butene-1,4-diols with 2-(1-Alkynyl)-2-alken-1-ones
    Yao, Tuanli
    She, Jun-E
    Li, Tao
    Qin, Xiangyang
    ORGANIC LETTERS, 2024, 26 (10) : 2018 - 2022
  • [18] Ammonium Acetate-Promoted One-Pot Tandem Aldol Condensation/Aza-Addition Reactions: Synthesis of 2,3,6,7-Tetrahydro-1H-pyrrolo[3,2-c] pyridin-4(5H)-ones
    Zhang, Zhiguo
    Gao, Xiaolong
    Wan, Yameng
    Huang, Yuanyuan
    Huang, Guoqing
    Zhang, Guisheng
    ACS OMEGA, 2017, 2 (10): : 6844 - 6851
  • [19] A fast and highly efficient one-pot synthesis of novel isoxazolyl pyrido[2,3-b][1,4]oxazin-2(3H)-ones via Smiles rearrangement using task-specific ionic liquid [HMIm]BF4 as green solvent
    Reddy, Modugu Nagi
    Kumar, Pittala Praveen
    Rajanarendar, Eligeti
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2017, 10 (01) : 48 - 53
  • [20] 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
    Anastasia A. Fesenko
    Mikhail S. Grigoriev
    Anatoly D. Shutalev
    Chemistry of Heterocyclic Compounds, 2023, 59 : 793 - 798
123