New Efficient Synthesis of 5-Ethoxyoxazoles and Oxazolo[3,2-c]quinazolines via Aza-Wittig Reaction

被引:19
|
作者
Huang, Nian-Yu [1 ]
Nie, Yi-Bo [1 ]
Ding, Ming-Wu [1 ]
机构
[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China
基金
中国国家自然科学基金;
关键词
oxazole; oxazolo[3,2-c]quinazoline; aza Wittig reaction; carbodiimide; imidoyl chloride; IMINOPHOSPHORANE-MEDIATED SYNTHESIS; FACILE SYNTHESIS; OXAZOLES; ROUTE;
D O I
10.1055/s-0028-1087562
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-Ethoxyoxazoles or 2-acylamino propanoates were synthesized by aza-Wittig reaction of iminophosphorane with acyl chloride in the presence of triethylamine. Reactions of 5-alkoxyoxazole with triphenyphosphine produced iminophosphoranes. A tandem aza-Wittig reaction of iminophosphorane with isocyanate or carbon disulfide generated oxazolo[3,2-c]quinazolines in satisfactory yields.
引用
收藏
页码:611 / 614
页数:4
相关论文
共 50 条
  • [1] NEW METHODOLOGY FOR THE PREPARATION OF QUINAZOLINE DERIVATIVES VIA TANDEM AZA-WITTIG/HETEROCUMULENE-MEDIATED ANNULATION - SYNTHESIS OF 4(3H)-QUINAZOLINONES, BENZIMIDAZO[1,2-C]QUINAZOLINES, QUINAZOLINO[3,2-A]QUINAZOLINES AND BENZOTHIAZOLO[3,2-C]QUINAZOLINES
    MOLINA, P
    ALAJARIN, M
    VIDAL, A
    FOCESFOCES, MD
    CANO, FH
    TETRAHEDRON, 1989, 45 (13) : 4263 - 4286
  • [2] Synthesis of Tritylones via Cascade Reaction of Arynes with 5-Ethoxyoxazoles
    Garg, Parul
    Upreti, Ganesh Chandra
    Singh, Anand
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (11): : 7219 - 7228
  • [3] A NEW EFFICIENT SYNTHESIS OF IMIDAZOLINONES AND QUINAZOLINONE BY INTRAMOLECULAR AZA-WITTIG REACTION
    TAKEUCHI, H
    HAGIWARA, S
    EGUCHI, S
    TETRAHEDRON, 1989, 45 (20) : 6375 - 6386
  • [4] New Efficient Synthesis of 1,4-Benzodiazepin-5-ones by Catalytic Aza-Wittig Reaction
    Wang, Long
    Qin, Ru-Qing
    Yan, Hong-Ye
    Ding, Ming-Wu
    SYNTHESIS-STUTTGART, 2015, 47 (22): : 3522 - 3528
  • [5] A NEW ROUTE TO QUINAZOLINONES VIA INTRAMOLECULAR AZA-WITTIG REACTION
    TAKEUCHI, H
    EGUCHI, S
    TETRAHEDRON LETTERS, 1989, 30 (25) : 3313 - 3314
  • [6] Efficient Synthesis of Fused Pyrimidine Derivatives with Biological Activity via Aza-Wittig Reaction
    Ren Qingyun
    Tan Xiaosong
    He Hongwu
    CURRENT ORGANIC SYNTHESIS, 2011, 8 (05) : 752 - 763
  • [7] Efficient Synthesis of Quinolines via a Knoevenagel/Staudinger/aza-Wittig Sequence
    Qu, Feng
    He, Ping
    Hu, Ruo-Fei
    Cheng, Xiao-Hong
    Wang, Song
    Wu, Jing
    SYNTHETIC COMMUNICATIONS, 2015, 45 (24) : 2802 - 2809
  • [8] New efficient synthesis of 2-substituted benzothieno[3,2-d]pyrimidin-4(3H)-ones via a tandem aza-Wittig reaction
    Xu, Sheng-Zhen
    Hu, Yang-Gen
    Ding, Ming-Wu
    SYNTHESIS-STUTTGART, 2006, (24): : 4180 - 4186
  • [9] New efficient synthesis of 1,2,4-trisubstituted imidazoles and imidazo[1,2-c] quinazolines by a tandem aza-Wittig/electrocyclic ring-closure process
    Nie, Yi-Bo
    Duan, Zhuan
    Ding, Ming-Wu
    TETRAHEDRON, 2012, 68 (04) : 965 - 971
  • [10] Theoretical prediction on efficient formation of imino acid via an aza-Wittig reaction
    Lu, WC
    Zhang, RQ
    Zang, QJ
    Wong, NB
    JOURNAL OF PHYSICAL CHEMISTRY B, 2003, 107 (09): : 2061 - 2067