New Efficient Synthesis of 2,3,5-Trisubstituted Pyrimidin-4(3H)-ones from Baylis-Hillman Adducts

被引:12
|
作者
Zhong, Ying [1 ]
Wu, Lei [1 ]
Ding, Ming-Wu [1 ]
机构
[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China
来源
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 19期
基金
中国国家自然科学基金;
关键词
azides; heterocycles; cyclizations; Wittig reactions; amines; alcohols; phenols; DERIVATIVES; ANTAGONISTS; CONSTRUCTION;
D O I
10.1055/s-0032-1317034
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Azides obtained from Baylis-Hillman adducts were treated with triphenylphosphine to give the corresponding iminophosphoranes that underwent aza-Wittig reactions with aryl isocyanates and then reacted with amines, alcohol, or phenols in the presence of catalytic amounts of sodium alkoxide or potassium carbonate to give the corresponding 2,3,5-trisubstituted pyrimidin-4(3H)-ones directly in good yields.
引用
收藏
页码:3085 / 3089
页数:5
相关论文
共 50 条
  • [31] Highly Regioselective Synthesis of 3,6-Disubstituted 2-(Methylsulfanyl)pyrimidin-4(3H)-ones
    dos Santos, Josiane M.
    da Silveira, Alessandra S.
    Souza, Laura A.
    Lobo, Marcio M.
    Bonacorso, Helio G.
    Martins, Marcos A. P.
    Zanatta, Nilo
    SYNTHESIS-STUTTGART, 2015, 47 (24): : 3947 - 3955
  • [32] Regioselective synthesis of 1,3,4,5-tetrasubstituted pyrazoles from Baylis-Hillman adducts
    Lee, KY
    Kim, JM
    Kim, JN
    TETRAHEDRON LETTERS, 2003, 44 (35) : 6737 - 6740
  • [33] An approach to substituted dihydroisoquinolin-1(2H)-ones from Baylis-Hillman adducts
    Coelho, F
    Veronese, D
    Lopes, ECS
    Rossi, RC
    TETRAHEDRON LETTERS, 2003, 44 (30) : 5731 - 5735
  • [34] PHOSPHORUS PENTOXIDE IN ORGANIC-SYNTHESIS .3. A NEW SYNTHESIS OF "PYRIDOL[2,3-D]-PYRIMIDIN-4(3H)-ONES
    ANDRESEN, OR
    PEDERSEN, EB
    LIEBIGS ANNALEN DER CHEMIE, 1982, (05): : 1012 - 1015
  • [35] Vilsmeier Reaction of 3-Aminopropenamides: One-Pot Synthesis of Pyrimidin-4(3H)-ones
    Zhang, Rui
    Zhang, Dingyuan
    Liang, Yongjiu
    Zhou, Guangyuan
    Dong, Dewen
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08): : 2880 - 2883
  • [36] Synthesis of functionalized 3-spirocyclopropane-2-indolones from isomerised Baylis-Hillman adducts of isatin
    Shanmugam, P
    Vaithiyanathan, V
    Viswambharan, B
    TETRAHEDRON, 2006, 62 (18) : 4342 - 4348
  • [37] Facile synthesis of 1,2,3,4-tetrasubstituted pyrroles from Baylis-Hillman adducts
    Kim, Seong Jin
    Kim, Hoo Sook
    Kim, Taek Hyeon
    Kim, Jae Nyoung
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2007, 28 (09) : 1605 - 1608
  • [38] Synthesis and antimalarial activity of Baylis-Hillman adducts from substituted 2-chloroquinoline-3-carboxaldehydes
    Srihari, Ejjirothu
    Kumar, Gangala Siva
    Kumar, Chebolu Naga Sesha Sai Pavan
    Seth, Ratnesh Kumar
    Biswas, Sukla
    Sridhar, Balasubramanian
    Rao, Vaidya Jayathirtha
    HETEROCYCLIC COMMUNICATIONS, 2011, 17 (3-4) : 111 - 119
  • [39] Synthesis and analgesic activity of 2-arylamino-3-aryl-5-phenyl-thieno [2,3-d] pyrimidin-4 (3H)-ones and 2-arylamino-3-aryl-7-phenyl-thieno [3,2-d] pyrimidin-4 (3H)-ones
    Rathod, IS
    Patel, HU
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 15 (03) : 271 - 274
  • [40] A selective synthesis of 2-alkylamino thieno[2,3-d]pyrimidin-4(3H)-ones
    Sun, Shao-Fa
    Yang, Xu-Hong
    HETEROCYCLIC COMMUNICATIONS, 2007, 13 (06) : 367 - 370