共 25 条
One-Pot Highly Regioselective Synthesis of Indole-Fused Pyridazino[4,5-b][1,4]benzoxazepin-4(3H)-ones by a Smiles Rearrangement
被引:8
作者:

Jiang, Xiaolei
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机构:
Linyi Univ, Sch Chem & Chem Engn, Linyi 276005, Shandong, Peoples R China Linyi Univ, Sch Chem & Chem Engn, Linyi 276005, Shandong, Peoples R China

Hu, Fangdong
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Linyi Univ, Sch Chem & Chem Engn, Linyi 276005, Shandong, Peoples R China Linyi Univ, Sch Chem & Chem Engn, Linyi 276005, Shandong, Peoples R China
机构:
[1] Linyi Univ, Sch Chem & Chem Engn, Linyi 276005, Shandong, Peoples R China
来源:
关键词:
indoles;
indolopyridazinobenzoxazepinanes;
regioselectivity;
polycyclic heterocycles;
Smiles rearrangement;
DIBENZOXAZEPINONES;
CONSTRUCTION;
D O I:
10.1055/s-0037-1609338
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
A simple and convenient synthesis of indole-fused pyridazino[4,5-b][1,4]benzoxazepin-4(3H)-ones is described. A range of 2-(1Hindol-2-yl)phenols and 4,5-dichloropyridazln-3-ones are compatible with this reaction. A Smiles rearrangement is proposed as a key step in the highly regioselective construction of the products. The easy availability of the starting materials makes this an appealing method in organic synthesis.
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页码:1207 / 1210
页数:4
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共 25 条
[1]
Antiproliferative and Differentiating Activities of a Novel Series of Histone Deacetylase Inhibitors
[J].
Binaschi, Monica
;
Boldetti, Andrea
;
Gianni, Maurizio
;
Maggi, Carlo Alberto
;
Gensini, Martina
;
Bigioni, Mario
;
Parlani, Massimo
;
Giolitti, Alessandro
;
Fratelli, Maddalena
;
Valli, Claudia
;
Terao, Mineko
;
Garattini, Enrico
.
ACS MEDICINAL CHEMISTRY LETTERS,
2010, 1 (08)
:411-415

Binaschi, Monica
论文数: 0 引用数: 0
h-index: 0
机构:
Menarini Ric SpA, I-00040 Rome, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy

Boldetti, Andrea
论文数: 0 引用数: 0
h-index: 0
机构:
Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy

Gianni, Maurizio
论文数: 0 引用数: 0
h-index: 0
机构:
Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy

Maggi, Carlo Alberto
论文数: 0 引用数: 0
h-index: 0
机构:
Menarini Ric SpA, I-00040 Rome, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy

Gensini, Martina
论文数: 0 引用数: 0
h-index: 0
机构:
Menarini Ric SpA, I-00040 Rome, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy

Bigioni, Mario
论文数: 0 引用数: 0
h-index: 0
机构:
Menarini Ric SpA, I-00040 Rome, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy

Parlani, Massimo
论文数: 0 引用数: 0
h-index: 0
机构:
Menarini Ric SpA, I-00040 Rome, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy

Giolitti, Alessandro
论文数: 0 引用数: 0
h-index: 0
机构:
Menarini Ric SpA, I-00040 Rome, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy

Fratelli, Maddalena
论文数: 0 引用数: 0
h-index: 0
机构:
Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy

Valli, Claudia
论文数: 0 引用数: 0
h-index: 0
机构:
Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy

Terao, Mineko
论文数: 0 引用数: 0
h-index: 0
机构:
Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy

Garattini, Enrico
论文数: 0 引用数: 0
h-index: 0
机构:
Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy Ist Ric Farmacol Mario Negri, Mol Biol Lab, I-20156 Milan, Italy
[2]
An efficient synthesis of [1,4]pyridazinooxazine[3,4-a]tetrahydro isoquinolines
[J].
Cho, SD
;
Park, YD
;
Kim, JJ
;
Joo, WH
;
Shiro, M
;
Esser, L
;
Falck, JR
;
Ahn, CJ
;
Shin, DS
;
Yoon, YJ
.
TETRAHEDRON,
2004, 60 (17)
:3763-3773

Cho, SD
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea

Park, YD
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea

Kim, JJ
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea

Joo, WH
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea

Shiro, M
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea

Esser, L
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea

Falck, JR
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea

Ahn, CJ
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea

Shin, DS
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea

Yoon, YJ
论文数: 0 引用数: 0
h-index: 0
机构:
Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea
[3]
A one-pot synthesis of pyrido[2,3-b][1,4]oxazin-2-ones
[J].
Cho, SD
;
Park, YD
;
Kim, JJ
;
Lee, SG
;
Ma, C
;
Song, SY
;
Joo, WH
;
Falck, JR
;
Shiro, M
;
Shin, DS
;
Yoon, YJ
.
JOURNAL OF ORGANIC CHEMISTRY,
2003, 68 (20)
:7918-7920

Cho, SD
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea

Park, YD
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea

Kim, JJ
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea

Lee, SG
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea

Ma, C
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea

Song, SY
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea

Joo, WH
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea

Falck, JR
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea

Shiro, M
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea

Shin, DS
论文数: 0 引用数: 0
h-index: 0
机构:
Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea

Yoon, YJ
论文数: 0 引用数: 0
h-index: 0
机构: Gyeongsang Natl Univ, Dept Chem, Chinju 660701, South Korea
[4]
Novel synthesis of pyridazino[4,5-b][1,4]oxazin-3,8-diones
[J].
Cho, SD
;
Song, SY
;
Park, YD
;
Kim, JJ
;
Joo, WH
;
Shiro, M
;
Falck, JR
;
Shin, DS
;
Yoon, YJ
.
TETRAHEDRON LETTERS,
2003, 44 (50)
:8995-8998

Cho, SD
论文数: 0 引用数: 0
h-index: 0
机构: Changwon Natl Univ, Dept Chem & Biol, Chang Won 641773, South Korea

Song, SY
论文数: 0 引用数: 0
h-index: 0
机构: Changwon Natl Univ, Dept Chem & Biol, Chang Won 641773, South Korea

Park, YD
论文数: 0 引用数: 0
h-index: 0
机构: Changwon Natl Univ, Dept Chem & Biol, Chang Won 641773, South Korea

Kim, JJ
论文数: 0 引用数: 0
h-index: 0
机构: Changwon Natl Univ, Dept Chem & Biol, Chang Won 641773, South Korea

Joo, WH
论文数: 0 引用数: 0
h-index: 0
机构: Changwon Natl Univ, Dept Chem & Biol, Chang Won 641773, South Korea

Shiro, M
论文数: 0 引用数: 0
h-index: 0
机构: Changwon Natl Univ, Dept Chem & Biol, Chang Won 641773, South Korea

Falck, JR
论文数: 0 引用数: 0
h-index: 0
机构: Changwon Natl Univ, Dept Chem & Biol, Chang Won 641773, South Korea

Shin, DS
论文数: 0 引用数: 0
h-index: 0
机构: Changwon Natl Univ, Dept Chem & Biol, Chang Won 641773, South Korea

Yoon, YJ
论文数: 0 引用数: 0
h-index: 0
机构:
Changwon Natl Univ, Dept Chem & Biol, Chang Won 641773, South Korea Changwon Natl Univ, Dept Chem & Biol, Chang Won 641773, South Korea
[5]
SAR study of 2,3,4,14b-tetrahydro-1H-dibenzo[b,f] pyrido[ 1,2-d][1,4] oxazepines as progesterone receptor agonists
[J].
Dols, Paul P. M. A.
;
Folmer, Brigitte J. B.
;
Hamersma, Hans
;
Kuil, Cor W.
;
Lucas, Hans
;
Ollero, Lourdes
;
Rewinkel, Jos B. M.
;
Hermkens, Pedro H. H.
.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,
2008, 18 (04)
:1461-1467

Dols, Paul P. M. A.
论文数: 0 引用数: 0
h-index: 0
机构:
NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands

Folmer, Brigitte J. B.
论文数: 0 引用数: 0
h-index: 0
机构:
NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands

Hamersma, Hans
论文数: 0 引用数: 0
h-index: 0
机构:
NV Organon, Dept Mol Design & Informat, NL-5340 BH Oss, Netherlands NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands

Kuil, Cor W.
论文数: 0 引用数: 0
h-index: 0
机构:
NV Organon, Dept Mol Pharmacol, NL-5340 BH Oss, Netherlands NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands

Lucas, Hans
论文数: 0 引用数: 0
h-index: 0
机构:
NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands

Ollero, Lourdes
论文数: 0 引用数: 0
h-index: 0
机构:
NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands

Rewinkel, Jos B. M.
论文数: 0 引用数: 0
h-index: 0
机构:
NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands

Hermkens, Pedro H. H.
论文数: 0 引用数: 0
h-index: 0
机构:
NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands NV Organon, Dept Med Chem, NL-5340 BH Oss, Netherlands
[6]
Design, synthesis and SAR of phenylamino-substituted 5,11-dihydro-dibenzo[a,d]cyclohepten-10-ones and 11H-dibenzo[b,f]oxepin-10-ones as p38 MAP kinase inhibitors
[J].
Dorn, Angelika
;
Schattel, Verena
;
Laufer, Stefan
.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,
2010, 20 (10)
:3074-3077

Dorn, Angelika
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tubingen, Inst Pharm, Dept Pharmaceut & Med Chem, D-72076 Tubingen, Germany Univ Tubingen, Inst Pharm, Dept Pharmaceut & Med Chem, D-72076 Tubingen, Germany

Schattel, Verena
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tubingen, Inst Pharm, Dept Pharmaceut & Med Chem, D-72076 Tubingen, Germany Univ Tubingen, Inst Pharm, Dept Pharmaceut & Med Chem, D-72076 Tubingen, Germany

Laufer, Stefan
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tubingen, Inst Pharm, Dept Pharmaceut & Med Chem, D-72076 Tubingen, Germany Univ Tubingen, Inst Pharm, Dept Pharmaceut & Med Chem, D-72076 Tubingen, Germany
[7]
Analogues of Morphanthridine and the Tear Gas Dibenz[b,f][1,4]oxazepine (CR) as Extremely Potent Activators of the Human Transient Receptor Potential Ankyrin1 (TRPA1) Channel
[J].
Gijsen, Harrie J. M.
;
Berthelot, Didier
;
Zaja, Mirko
;
Brone, Bert
;
Geuens, Ivo
;
Mercken, Marc
.
JOURNAL OF MEDICINAL CHEMISTRY,
2010, 53 (19)
:7011-7020

Gijsen, Harrie J. M.
论文数: 0 引用数: 0
h-index: 0
机构:
Johnson & Johnson Pharmaceut Res & Dev, Dept Med Chem, B-2340 Beerse, Belgium Johnson & Johnson Pharmaceut Res & Dev, Dept Med Chem, B-2340 Beerse, Belgium

Berthelot, Didier
论文数: 0 引用数: 0
h-index: 0
机构:
Johnson & Johnson Pharmaceut Res & Dev, Dept Med Chem, B-2340 Beerse, Belgium Johnson & Johnson Pharmaceut Res & Dev, Dept Med Chem, B-2340 Beerse, Belgium

Zaja, Mirko
论文数: 0 引用数: 0
h-index: 0
机构:
Johnson & Johnson Pharmaceut Res & Dev, Dept Med Chem, B-2340 Beerse, Belgium Johnson & Johnson Pharmaceut Res & Dev, Dept Med Chem, B-2340 Beerse, Belgium

Brone, Bert
论文数: 0 引用数: 0
h-index: 0
机构:
Johnson & Johnson Pharmaceut Res & Dev, Neurosci, B-2340 Beerse, Belgium Johnson & Johnson Pharmaceut Res & Dev, Dept Med Chem, B-2340 Beerse, Belgium

Geuens, Ivo
论文数: 0 引用数: 0
h-index: 0
机构:
Johnson & Johnson Pharmaceut Res & Dev, Neurosci, B-2340 Beerse, Belgium Johnson & Johnson Pharmaceut Res & Dev, Dept Med Chem, B-2340 Beerse, Belgium

Mercken, Marc
论文数: 0 引用数: 0
h-index: 0
机构:
Johnson & Johnson Pharmaceut Res & Dev, Neurosci, B-2340 Beerse, Belgium Johnson & Johnson Pharmaceut Res & Dev, Dept Med Chem, B-2340 Beerse, Belgium
[8]
8-CHLORODIBENZ[B,F][1,4]OXAZEPINE-10(11H)-CARBOXYLIC ACID, 2-[3-[2-(FURANYLMETHYL)THIO]-1-OXOPROPYL]HYDRAZIDE (SC-51322) - A POTENT PGE(2) ANTAGONIST AND ANALGESIC
[J].
HALLINAN, EA
;
STAPELFELD, A
;
SAVAGE, MA
;
REICHMAN, M
.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,
1994, 4 (03)
:509-514

HALLINAN, EA
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry Searle, Skokie, IL 60077

STAPELFELD, A
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry Searle, Skokie, IL 60077

SAVAGE, MA
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry Searle, Skokie, IL 60077

REICHMAN, M
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry Searle, Skokie, IL 60077
[9]
Copper-Catalyzed Cross-Coupling Interrupted by an Opportunistic Smiles Rearrangement: An Efficient Domino Approach to Dibenzoxazepinones
[J].
Kitching, Matthew O.
;
Hurst, Timothy E.
;
Snieckus, Victor
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2012, 51 (12)
:2925-2929

Kitching, Matthew O.
论文数: 0 引用数: 0
h-index: 0
机构:
Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

Hurst, Timothy E.
论文数: 0 引用数: 0
h-index: 0
机构:
Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

Snieckus, Victor
论文数: 0 引用数: 0
h-index: 0
机构:
Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada
[10]
Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety
[J].
Kochanowska-Karamyan, Anna J.
;
Hamann, Mark T.
.
CHEMICAL REVIEWS,
2010, 110 (08)
:4489-4497

Kochanowska-Karamyan, Anna J.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Mississippi, Dept Pharmacognosy, University, MS 38677 USA

Hamann, Mark T.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Mississippi, Dept Pharmacognosy, University, MS 38677 USA Univ Mississippi, Dept Pharmacognosy, University, MS 38677 USA