Transformation of 5,6,7,8-tetrahydro-2H-1-benzopyran-2,8-diones with hydrazines and hydrazoic acid:: Synthesis of 8-hydrazono-5,6,7,8-tetrahydro-2-oxo-2H-1-benzopyrans, pyrano[2,3-c]azepines and pyrido[2,3-c]azepines

被引：0

作者：

Trebse, P

Vranicar, L

Music, I

Polanc, S

Stevens, WC

Kocevar, M

机构：

[1] Univ Ljubljana, Fac Chem & Chem Technol, SI-1000 Ljubljana, Slovenia

[2] So Illinois Univ, Nucl Magnet Resonance Facil, Carbondale, IL 62901 USA

来源：

HETEROCYCLES | 2000年 / 53卷 / 05期

关键词：

Schmidt reaction; fused pyran-2-one; fused pyridine; lactam coumarin;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-(5,6,7,8-Tetrahydro-2,5-dioxo-2H-1-benzopyran-3-yl)benzamide (1a) reacts with nitrogen-containing nucleophiles (2) (hydrazines and hydroxylamine) to give the corresponding 8-hydrazono derivatives (3a-i) and the related hydroxyimino derivative (3j). The action of hydrazoic acid on 1a-b or 3a-b and 3e resulted in the formation of pyrano[2,3-c]azepines (4a-b). The pyranoazepine (4a) can be debenzoylated to 4b or transformed into pyrido[2,3-c]azepines (5a-b).

引用

页码：1111 / +

页数：11

共 50 条

[31] SYNTHESIS OF 2,3,4,6,7,8-HEXAHYDRO-5H-1-BENZOPYRAN-5-ONES AND 3-(6-OXO-1-CYCLOHEXENYL)ALKANOIC ACIDS BY REDUCTION OF 4,6,7,8-TETRAHYDRO-2H-1-BENZOPYRAN-2,5(3H)-DIONES
HOMBRECHER, H
MARGARETHA, P
TISSOT, P
HELVETICA CHIMICA ACTA, 1986, 69 (07) : 1681 - 1684
[32] SYNTHESIS OF TETRAHYDRO--6H-BENZO [4,5] PYRANO [2,3-C] PYRIDIN-6-ONE - NOVEL RING-SYSTEM
LOTZ, F
KRAATZ, U
KORTE, F
HETEROCYCLES, 1977, 8 : 115 - 118
[33] A SYNTHESIS OF 1-METHYL-2-OXO-3H-PYRROLO[2,3-C]PYRIDINE
FAITA, G
POZZI, G
RIGHETTI, PP
TACCONI, G
GAZZETTA CHIMICA ITALIANA, 1994, 124 (10): : 437 - 438
[34] SYNTHESIS OF 7-BENZYL-3-OXO-7H,1,2,3,4,5,6-HEXAHYDROPYRROLO[2,3-C]PYRIDAZINE
YAKHONTOV, LN
URITSKAYA, MY
GLUSHKOV, RG
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1976, (08): : 1127 - 1131
[35] REGIOSELECTIVE SYNTHESIS OF 2H-PYRANO[3,2-C]BENZOPYRAN-5H-ONE AND 3H-PYRANO[2,3-C]BENZOPYRAN-5H-ONE
MAJUMDAR, KC
KHAN, AT
DE, RN
SYNTHETIC COMMUNICATIONS, 1988, 18 (13) : 1589 - 1595
[36] A direct conversion of 5,6,7,8-tetrahydro-2H-1-benzo-pyran-2,5-diones into substituted 1-amino-5,6,7,8-tetrahydroquinoline-2,5-diones
Trebse, P
Polanc, S
Kocevar, M
HETEROCYCLES, 2003, 59 (01) : 129 - 136
[37] CHEMICAL AND PHARMACOLOGICAL RESEARCH ON PYRAN DERIVATIVES .7. DERIVATIVES OF NAPHTHO[1',2'-5,6]PYRANO[2,3-C]PYRAZOLE AND 12H-NAPHTHO[1',2'-5,6]PYRANO[2,3-D]PYRIMIDINE
ROMA, G
VIGEVANI, E
MAZZEI, M
ERMILI, A
FARMACO-EDIZIONE SCIENTIFICA, 1977, 32 (01): : 40 - 53
[38] Organocatalyzed synthesis of 2-amino-8-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles
Ding, Derong
Zhao, Cong-Gui
TETRAHEDRON LETTERS, 2010, 51 (09) : 1322 - 1325
[39] SYNTHESIS OF 1H-PYRANO [2,3-C] PYRAZOLE-4-ONES
KHAN, MA
PAGOTTO, MC
ELLIS, GP
HETEROCYCLES, 1977, 6 (07) : 983 - 986
[40] Synthesis of 5-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridines and 5-phenyl-6,7,8,9-tetrahydro-5H-pyrido[3,2-c]azepines as potential D1 receptor ligands
Hussenether, T
Troschütz, R
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2004, 41 (06) : 857 - 865

← 1 2 3 4 5 →