Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data

被引：17

作者：

Datterl, Barbara ^{[1
]}

Troestner, Nicole ^{[1
]}

Kucharski, Dorota ^{[1
]}

Holzer, Wolfgang ^{[1
]}

机构：

[1] Univ Vienna, Dept Drug & Nat Product Synth, Fac Life Sci, A-1090 Vienna, Austria

来源：

MOLECULES | 2010年 / 15卷 / 09期

关键词：

pyrazolones; 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones; cyclization; Lawesson's reagent; NMR spectroscopy; DERIVATIVES; RING; C-13; ASSIGNMENT; INSIGHTS; SYSTEMS;

D O I：

10.3390/molecules15096106

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3- methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c: 6,5-c] dipyrazol-4(7H)-ones by treatment with K2CO3/DMF. The latter were converted into the corresponding thiones upon reaction with Lawesson's reagent. Detailed NMR spectroscopic investigations (H-1, C-13, N-15) of the ring systems and their precursors are presented.

引用

页码：6106 / 6126

页数：21

共 50 条

[1] SYNTHESIS OF 1H-PYRANO [2,3-C] PYRAZOLE-4-ONES
KHAN, MA
PAGOTTO, MC
ELLIS, GP
HETEROCYCLES, 1977, 6 (07) : 983 - 986
[2] Pyranopyrazoles III synthesis of 1H-pyrano[2,3-c]pyrazol-4-ones
Khan, MA
Ellis, GP
Pagotto, MC
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (01) : 193 - 197
[3] SYNTHESIS AND BIOLOGICAL EVALUATION OF SPIRO[INDOLINE-3,4′-PYRANO[2,3-C:6,5-C′]DIPYRAZOL]-2-ONES IN THE PRESENCE OF SBA-Pr-SO3H AS A NANOCATALYST
Ziarani, Ghodsi Mohammadi
Moradi, Razieh
Lashgari, Negar
Badiei, Alireza
Soorki, Ali Abolhasani
QUIMICA NOVA, 2015, 38 (09): : 1167 - 1171
[4] Ag NPs decked GO composite as a competent and reusable catalyst for 'ON WATER' chemoselective synthesis of pyrano[2,3-c:6,5-c′]dipyrazol]-2-ones
Dandia, Anshu
Gupta, Shyam L.
Indora, Aayushi
Saini, Pratibha
Parewa, Vijay
Rathore, Kuldeep S.
TETRAHEDRON LETTERS, 2017, 58 (12) : 1170 - 1175
[5] An efficient approach to heterocyclic analogues of xanthone:: A short synthesis of all possible pyrido[5,6]pyrano[2,3-c]pyrazol-4(1H)-ones
Eller, Gernot A.
Wimmer, Veronika
Haring, Andreas W.
Holzer, Wolfgang
SYNTHESIS-STUTTGART, 2006, (24): : 4219 - 4229
[6] PYRANOPYRAZOLES .2. SYNTHESIS AND REACTIONS OF 1H,6H-PYRANO[2,3-C]PYRAZOL-6-ONES
KHAN, MA
COSENZA, AG
ELLIS, GP
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (05) : 1077 - 1085
[7] Mass Spectrometry of Substituted 1H,6H-Pyrano[2,3-c]pyrazol-6-ones
Asif, Nadia
Chaudhry, Faryal
Khan, Muhammad Naeem
Cosenza, Alina Guerra
Ellis, Gwynn Penant
Khan, Misbahul Ain
Munawar, Munawar Ali
Iqbal, Sana
Aslam, Noreen
ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (17) : 9639 - 9642
[8] Unusual ring contraction of 3H-pyrano[2,3-c] quinolin-5(6H)-ones to furo[2,3-c]quinolin-4(5H)-ones
Majumdar, KC
Kundu, AK
Biswas, P
HETEROCYCLES, 1999, 51 (03) : 471 - 474
[9] 8-AMINO-1H-PYRIMIDO[4,5-C]-1,2-DIAZEPIN-6(7H)-ONES - VERSATILE INTERMEDIATES FOR HETEROCYCLIC TRANSFORMATIONS
MORRISON, RW
MALLORY, WR
STYLES, VL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1977, 174 (SEP): : 9 - 9
[10] A NOVEL ONE-POT SYNTHESIS OF SUBSTITUTED 5-BENZOYL-1H,6H-PYRANO[2,3-C]PYRAZOLONE AND 5-ACETYLAMINO-1H, 6H-PYRANO[2,3-C]PYRAZOLONE
AHLUWALIA, VK
GARG, VK
SHARMA, MK
SHARMA, R
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1993, 32 (09): : 960 - 962

← 1 2 3 4 5 →