ALTERNATIVE SYNTHESIS OF 6-(3-METHOXYBENZYL)PYRAZIN-2(1H)-ONE - SYNTHESIS OF INDENO[1,2-B]PYRAZIN-2-ONES - CRYSTAL-STRUCTURES OF 5-ACETOXY-1-BENZYL-4-TERT-BUTOXYCARBONYL-6-(3-METHOXYBENZYLIDENE)PIPERAZIN-2-ONE, 1-BENZYL-4-TERT-BUTOXYCARBONYL-7-METHOXY-1,3,4,4A-TETRAHYDROINDENO[1,2-B]PYRAZIN-2-ONE AND 1-BENZYL-4-TERT-BUTOXYCARBONYL-7-METHOXY-1,3,4,9-TETRAHYDROINDENO-[1,2-B]PYRAZIN-2-ONE

被引：11
作者：
PETERS, DA [1 ]
BEDDOES, RL [1 ]
JOULE, JA [1 ]
机构：
[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCS,ENGLAND
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 11期
关键词：
D O I：
10.1039/p19930001217
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1-Acetyl-3-(3-methoxybenzylidene)piperazine-2,5-dione 7a was converted via a 7-step sequence into 6-(3-methoxybenzyl)pyrazin-2(1H)-one 2a. Treatment of 1-benzyl-4-tert-butoxycarbonyl-5-hydroxy-6-(3-methoxybenzylidene)piperazin-2-one 8a with acids results in cyclisation to indeno[1,2-b]pyrazin-2-ones, 9a, 9b or 11. The X-ray crystal structure determinations of 5-acetoxy-1-benzyl-4-tert-butoxycarbonyl-6-(3-methoxybenzylidene)piperazin-2-one, 8b, 1-benzyl-4-tert-butoxycarbonyl-7-methoxy-1,3,4,4a-tetrahydroindeno[1,2-b]pyrazin-2-one, 9b and 1-benzyl-4-tert-butoxycarbonyl-7-methoxy-1,3,4,9-tetrahydroindeno[1,2-b] pyrazin-2-one, 11 are described.
引用
收藏
页码：1217 / 1224
页数：8
相关论文
共 50 条
[21]   Chemical Properties of 3-tert-Butyl-2-oxo-1,2-dihydro-pyrrolo[1,2-b][1,2,4]triazine-6-carboxylates [J].
Ivanov, S. M. ;
Koltun, D. S. ;
Kolotyrkina, N. G. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (04) :611-622
[22]   Chemical Properties of 3-tert-Butyl-2-oxo-1,2-dihydro­pyrrolo[1,2-b][1,2,4]triazine-6-carboxylates [J].
S. M. Ivanov ;
D. S. Koltun ;
N. G. Kolotyrkina .
Russian Journal of Organic Chemistry, 2023, 59 :611-622
[23]   Synthesis of substituted imidazo[1,2-b]-1,2,4-triazolo[4,3-d]-1,2,4-triazepine and 4H-imidazo[1,2-b]-1,2,4-triazino[4,3-d]-1,2,4-triazepin-7-one [J].
Kruglenko, VP ;
Povstyanoy, MV ;
Klyuev, NA ;
Idzikovsky, VA .
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1997, (10) :1420-1421
[24]   Synthesis of substituted imidazo[1,2-b]-1,2,4-triazolo[4,3-d]-1,2,4-triazepine and 4H-imidazo[1,2-b]-1,2,4-triazino[4,3-d]-1,2,4-triazepin-7-one [J].
Chem. Heterocycl. Compd., 10 (1238-1239)
[25]   Synthesis of substituted imidazo[1,2-b]-1,2,4-triazolo[4,3-d]-1,2,4-triazepine and 4H-imidazo[1,2-b]-1,2,4-triazino[4,3-d]-1,2,4-triazepin-7-one [J].
Kruglenko V.P. ;
Povstyanoi M.V. ;
Klyuev N.A. ;
Idzikovskii V.A. .
Chemistry of Heterocyclic Compounds, 1997, 33 (10) :1238-1239
[26]   Crystal structure of 1 ',1 ''-dimethyl-4 '-(4-cholorophenyl)dispiro[11H-indeno[1,2-b]quinoxaline-11,2 '-pyrrolidine-3 ',3 ''-piperidin]-4 ''-one [J].
Nagalakshmi, R. A. ;
Suresh, J. ;
Malathi, K. ;
Kumar, R. Ranjith ;
Lakshman, P. L. Nilantha .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 :O68-U258
[27]   Synthesis of 4-(2H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one via Ring-Switching Hydrazinolysis of 5-Ethoxymethylidenethiazolo [3,2-b][1,2,4]triazol-6-one [J].
Holota, Serhii ;
Shylych, Yaroslav ;
Derkach, Halyna ;
Karpenko, Olexandr ;
Gzella, Andrzej ;
Lesyk, Roman .
MOLBANK, 2018, (04)
[28]   SYNTHESIS OF PYRIDO[1,2-B][2,4]BENZODIAZEPIN-6(11H)-ONE AND RELATED COMPOUNDS [J].
DAVIS, M ;
KNOWLES, P ;
SHARP, BW ;
WALSH, RJA ;
WOOLDRID.KR .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (13) :2449-&
[29]   A π-stacked chain of hydrogen-bonded dimers in 3-tert-butyl-1-(4-chlorophenyl)-4-phenylindeno[1,2-b]pyrazolo[4,3-e]pyridin-5(1H)-one and a π-stacked sheet of hydrogen-bonded chains in 3-tert-butyl-1-(4-chlorophenyl)-4-(4-methoxyphenyl)indeno[1,2-b]pyrazolo[4,3-e]pyridin-5(1H)-one [J].
Portilla, Jaime ;
Lizarazo, Carolina ;
Cobo, Justo ;
Glidewell, Christopher .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2011, 67 :O479-O483
[30]   Synthesis of ethyl 2-methyl-4-aryl-5-oxo-1H, 4H-indeno [1,2-b] dihydropyridine-3-carboxylates [J].
Edayadulla, N. ;
Ramesh, P. .
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 16 (04) :371-374
12345