Solid-Phase Synthesis and Chemical Properties of 2-(2-Amino/hydroxyethyl)-1-aryl-3,4-dihydropyrazino[1, 2-b]indazol-2-iums

被引：12

作者：

Koci, Jan ^{[1
]}

Krchnak, Viktor ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2010年 / 12卷 / 01期

关键词：

POLYMER-SUPPORTED SYNTHESIS; INTRAMOLECULAR CYCLIZATION; EFFICIENT SYNTHESIS; N-ACYLIMINIUM; HETEROCYCLES; DESIGN; IONS; RING;

D O I：

10.1021/cc9001422

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Amino alcohols, diamines, benzenesulfonyl chlorides, and bromoketones were used to prepare polymer-supported 2-(2-(2-(amino/hydroxyl)ethylamino)ethyl)-3-benzoyl-2H-indazoles. Acid-mediated release yielded 2-((amino/hydroxyl)ethyl)-1-aryl-3,4-dihydropyrazino[1,2-b]indazole-2-iums. In neutral pH, iminiums spontaneously cyclized to complex fused heterocycles 3,6,9,10-tetraazatetracyclo[7.7.0.0(2,6).0(11,16)]hexadeca-11,13,15-trienes, 3-oxa-6,9,10-triazatetracyclo[7.7.0.0(2,6).0(11,16)]hexadeca-11,13,15-trienes, and 3,7,10,11-tetraazatetracyclo[8.7.0.0(2,7).0(12,17)]heptadeca-12,14,16-trienes. Transformations were carried out under mild conditions and tolerated diverse substitution patterns.

引用

页码：168 / 175

页数：8

共 50 条

[41] Solid-Phase Synthesis of 4,7,8-Trisubstituted 1,2,3,4-Tetrahydro-benzo[e][1,4]diazepin-5-ones
Lemrova, Barbora
Soural, Miroslav
[J]. ACS COMBINATORIAL SCIENCE, 2012, 14 (12) : 645 - 650
[42] Microwave-assisted Solid-phase Synthesis of N-substituted-2-aminobenzo[d][1,3] Thiazine Derivatives from a BOMBA Resin
Jun, Hee-Goo
Kim, Eun-Mi
Yoon, Hyo-Jeong
Gong, Young-Dae
[J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2017, 38 (03): : 334 - 341
[43] ANTI-CANCER DOCKING INVESTIGATIONS, ANTI-OXIDANT PROPERTIES AND MICROWAVE-ASSISTED SYNTHESIS OF 1-(4-((2-((7-HYDROXY-1, 8-NAPHTHYRIDIN-2-YL) AMINO)-6- PHENYLPYRIMIDIN-4-YL) AMINO)PHENYL)-3-ARYLPROP-2-EN-1-ONES
Reddy, B. Srinivasa
Rajeshwari, M.
Bhaskar, P.
Ramesh, D.
Laxminarayana, E.
[J]. HETEROCYCLIC LETTERS, 2021, 11 (04): : 627 - 637
[44] Green synthesis of novel spiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-2,3′(7′H)- dione, spiro[indeno[1,2-b]pyrazolo[4,3-e]pyridine-4,3′-indoline]-2′,3-dione, and spiro[benzo [h]pyrazolo[3,4-b]quinoline-7,3′-indoline]-2′,8(5H)-dione derivatives in aqueous medium
Wang, Zhansheng
Gao, Lingli
Xu, Zhongyun
Ling, Zhi
Qin, Yaqi
Rong, Liangce
Tu, Shu-Jiang
[J]. TETRAHEDRON, 2017, 73 (04) : 385 - 394
[45] Platinum(IV)-Catalyzed Regioselective Synthesis of Highly Substituted 4H-Cyclopenta[b]furans via Cascade Hetero- cyclization of 2-(1-Alkynyl)-3-aryl-2-propenals with Arylethenes
He, Ting
Gao, Pin
Zhao, Shu-Chun
Shi, You-Di
Liu, Xue-Yuan
Liang, Yong-Min
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (2-3) : 365 - 369
[46] Synthesis of novel spiro[chromeno[4′,3′:3,4]pyrazolo[1,2-b]phthalazine-7,3′-indoline]-2′,6,9,14-tetraone
Shalkouhi, Somaye Nikzad
Kefayati, Hassan
Shariati, Shahab
[J]. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (02) : 263 - 267
[47] Synthesis of benzo[6,7][1,4]diazepino[1,2-b]indazol-7(6H)-ones and benzo[f]pyrazolo[1,5-a][1,4]diazepin-4-ones via CuI/L-proline catalyzed intramolecular N2-arylation
Wang, Hong-Jun
Camara, Fatoumata
Haber, James C., Jr.
Mangette, John E.
[J]. TETRAHEDRON LETTERS, 2015, 56 (08) : 1030 - 1033
[48] Microwave assisted synthesis and antibacterial properties of some new 2-alkyl/aryl-(6-substitutedcoumarin-3-yl)imidazo[2,1-b][1,3,4]thiadiazoles
Jakhar, Anshu
Makrandi, J. K.
[J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2012, 51 (01): : 291 - 296
[49] Solid-phase Synthesis of Novel 7,8-Functionalized Pyrazolo[1,5-a][1,3,5]-2,4-Dithioxotriazine Derivatives on Dithiocarboxy Resin Bound Pyrazoles
Gong, Young-Dae
Kim, Jeong Guen
[J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (12): : 3085 - 3088
[50] Synthesis, anti-HIV activity and molecular modeling study of 3-aryl-6-adamantylmethyl-[1,2,4] triazolo[3,4-b][1,3,4] thiadiazole derivatives
Khan, Mahmood-ul-Hassan
Hameed, Shahid
Farman, Muhammad
Al-Masoudi, Najim A.
Stoeckli-Evans, Helen
[J]. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2015, 70 (08): : 609 - 616

← 1 2 3 4 5 →