ANNELATED PIPERAZINYL-7,8-DIHYDRO-6H-THIOPYRANO[3,2-D]PYRIMIDINES

被引：5
|
作者：
WU, MT
MACCOSS, M
IKELER, TJ
HIRSHFIELD, J
ARISON, BH
TOLMAN, RL
机构：
[1] Merck Sharp and Dohme Research Laboratories, Rahway, New Jersey
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1990年 / 27卷 / 06期
关键词：
D O I：
10.1002/jhet.5570270607
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tricyclic analogs of piperazinylthiopyrano[3,2‐d]pyrimidine hypoglycemic agents were prepared. The angular tricyclic systems, 8,9‐dihydro‐7H‐thiopyrano[2,3‐e][1,2,4]triazolo[4,3‐a]pyrimidine and 8,9‐dihydro‐7H‐tetrazolo[1,5‐a]thiopyrano[2,3‐e]pyrimidine derivatives were synthesized from 2,4‐dichloro‐7,8‐dihydro‐6H‐thiopyrano[3,2‐d]pyrimidine in three step sequences. Derivatives of the linear tricyclic system, 5,6‐dihydro‐7H‐thiopyrano[3,2‐d][1,2,4]triazolo[2,3‐a]pyrimidine, were prepared by condensation of 3‐amino‐1,2,4‐triazole with ethyl 3‐oxo‐tetrahydropyran‐2‐carboxylate. The tricyclic heteroaryl‐piperazines lacked significant hypoglycemic activity. Copyright © 1990 Journal of Heterocyclic Chemistry
引用
收藏
页码：1559 / 1563
页数：5
相关论文
共 50 条
  • [1] SYNTHESIS AND HYPOGLYCEMIC ACTIVITY OF 7,8-DIHYDRO-6H-THIOPYRANO[3,2-D]PYRIMIDINE DERIVATIVES AND RELATED-COMPOUNDS
    OHNO, S
    MIZUKOSHI, K
    KOMATSU, O
    KUNOH, Y
    NAKAMURA, Y
    KATOH, E
    NAGASAKA, M
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1986, 34 (10) : 4150 - 4165
  • [2] Identification of the 5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d] pyrimidine derivatives as highly selective PDE4B inhibitors
    Goto, Taiji
    Shiina, Akiko
    Murata, Takeshi
    Tomii, Masato
    Yamazaki, Takanori
    Yoshida, Ken-ichi
    Yoshino, Toshiharu
    Suzuki, Osamu
    Sogawa, Yoshitaka
    Mizukami, Kiyoshi
    Takagi, Nana
    Yoshitomi, Tomomi
    Etori, Maki
    Tsuchida, Hiroshi
    Mikkaichi, Tsuyoshi
    Nakao, Naoki
    Takahashi, Mizuki
    Takahashi, Hisashi
    Sasaki, Shigeki
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (03) : 893 - 899
  • [3] HYPOGLYCEMIC ACTIVITY OF MTP-1403 (2-AMINO-7,8-DIHYDRO-4-PIPERAZINYL-6H-THIOPYRANO 3,2-D PYRIMIDINE), A NEW HYPOGLYCEMIC AGENT
    KUNOH, Y
    IGUCHI, A
    GOTOH, M
    NOMURA, T
    SHIBATA, M
    SAKAMOTO, N
    ARCHIVES INTERNATIONALES DE PHARMACODYNAMIE ET DE THERAPIE, 1986, 280 (02): : 302 - 313
  • [4] CHROMOGENIC BEHAVIOR OF 7,8-DIHYDRO-6H-[1]BENZOPYRANO[3,2-D]XANTHENES
    FEICHTMAYR, F
    OBERLINNER, A
    LIEBIGS ANNALEN DER CHEMIE, 1979, (09): : 1337 - 1345
  • [5] Aminations and arylations by direct C-O activation for the design of 7,8-dihydro-6H-5,8-ethanopyrido[3,2-d]pyrimidines
    Laurent, Mazarine
    Bostyn, Stephane
    Marchivie, Mathieu
    Robin, Yves
    Routier, Sylvain
    Buron, Frederic
    RSC ADVANCES, 2021, 11 (32) : 19363 - 19377
  • [6] SYNTHESIS OF THIENO[3,2-D] AND SELENO[3,2-D] PYRIMIDINES
    AHKOW, G
    PAULMIER, C
    PASTOUR, P
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1974, 278 (26): : 1513 - 1514
  • [7] SYNTHESIS OF PYRANO, THIOPYRANO, AND PYRIDO[3,2-D]PYRAZOLES
    METWALLY, SA
    YOUNES, MI
    NOUR, AM
    HETEROCYCLES, 1986, 24 (06) : 1631 - 1636
  • [8] Synthesis of thiopyrano[4",3":4′,5′]pyrido[3′,2′:4, 5]furo[3,2-d]pyrimidines
    Ahmed, Essam Kh.
    Ameen, Mohamed A.
    CHINESE CHEMICAL LETTERS, 2010, 21 (06) : 669 - 673
  • [9] PYRIMIDINES .12. PROPARGYL CLAISEN REARRANGEMENT IN PYRIMIDINE SERIES - SYNTHESIS OF FURO[3,2-D]PYRIMIDINES AND PYRANO[3,2-D]PYRIMIDINES
    OTTER, BA
    SALUJA, SS
    FOX, JJ
    JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (18): : 2858 - &
  • [10] Studies on pyrimidine-annelated heterocycles:: Synthesis of pyrrolo [3,2-d] pyrimidines by amine oxide rearrangement
    Majumdar, KC
    Das, U
    Jana, NK
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11): : 3550 - 3553
12345