Novel synthetic approach to 6,7-dihydro-5H-imidazo[1,5-a]-pyrazin-8-ones

被引：14

作者：

Gopalsamy, A ^{[1
]}

Shi, MX ^{[1
]}

机构：

[1] Wyeth Res, Pearl River, NY 10965 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol035455i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel route to highly substituted chiral 6,7-dihydro-5H-imidazo[1,5-a]pyrazine-8-ones starting from Meldrum's acid is disclosed. The key features of the methodology are the incorporation of amino esters as a chiral pool and facile mild intramolecular cyclization to form the pyrazine ring. Incorporation of various substituents at different stages of the synthesis from various building block sets makes this methodology readily amenable to parallel synthesis.

引用

页码：3907 / 3909

页数：3

共 50 条

[21] Synthesis, structure characterization and preliminary biological evaluation of novel 5-alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives
Xie, Yong-Sheng
Pan, Xiao-Hong
Zhao, Bao-Xiang
Liu, Jin-Ting
Shin, Dong-Soo
Zhang, Jin-Hua
Zheng, Liang-Wen
Zhao, Jing
Miao, Jun-Ying
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (07) : 1367 - 1374
[22] NOVEL APPROACH TO THE SYNTHESIS OF 6,7-DIHYDROQUINAZOLINO[3,2-a]- [1,5]BENZODIAZEPIN-13(15)-ONES
Janciene, R.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 47 (03) : 390 - 391
[23] Novel approach to the synthesis of 6,7-dihydroquinazolino[3,2-a]- [1,5]benzodiazepin-13(15)-ones
R. Janciene
Chemistry of Heterocyclic Compounds, 2011, 47 : 390 - 391
[24] Triazolopyridines. Part 27. The preparation of novel 6,7-dihydro[1,2,3]triazolo[1,5-a]pyridines
Abarca, Belen
Adam, Rosa
Ballesteros, Rafael
ARKIVOC, 2010, : 319 - 327
[25] SYNTHESIS OF SOME 6,7-DIHYDRO-6-OXO-4H,8H-PYRAZOLO[1,5-E]-[1,3,5]OXADIAZEPINE DERIVATIVES
CHABANNET, M
GELIN, S
JOURNAL OF CHEMICAL RESEARCH-S, 1982, (01): : 20 - 21
[26] The Synthesis of Novel 7-(Substituted benzyl)-4,5-dihydro[1,2,3]triazolo[1,5-a]pyrazin-6(7H)-ones via Tandem Ugi-Huisgen Reactions
Pokhodylo, Nazariy T.
Tupychak, Mykola A.
Goreshnik, Evgeny A.
Obushak, Mykola D.
SYNTHESIS-STUTTGART, 2022, 55 (06): : 977 - 988
[27] SYNTHESIS OF NOVEL, SUBSTITUTED 4H-IMIDAZO[1,5-A][1,4]BENZODIAZEPINES
FRYER, RI
GU, ZQ
WANG, CG
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (07) : 1661 - 1669
[28] SYNTHESIS OF 6-PHENYLIMIDAZO[1,2-A]PYRAZIN-8-ONE AND 1-METHYL-6-PHENYLIMIDAZO[1,5-A]PYRAZIN-8-ONE VIA QUATERNARY INTERMEDIATES
DAVEY, DD
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19): : 4379 - 4381
[29] SYNTHESIS OF 6-PHENYLIMIDAZO[1,2-A]PYRAZIN-8-ONE AND 1-METHYL-6-PHENYLIMIDAZO[1,5-A]PYRAZIN-8-ONE VIA QUATERNARY INTERMEDIATES
DAVEY, DD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 194 : 299 - ORGN
[30] 2-[(ACYLAMINO)METHYL]-6-METHYLPYRIMIDIN-4(3H)-ONES - NOVEL PRECURSORS FOR THE SYNTHESIS OF IMIDAZO[1,5-A]PYRIMIDINES AND IMIDAZO[4,5-B]PYRIDINES
KATAGIRI, N
KOSHIHARA, A
ATSUUMI, S
KATO, T
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01): : 167 - 169

← 1 2 3 4 5 →