An organocatalytic rearrangement of 2-(N-alkyl-/aryl-)amino-4-oxo-4H-1-benzopyran-3-carbaldehyde

被引：4

作者：

Maiti, Sourav ^{[1
]}

Panja, Suman Kalyan ^{[1
]}

Bandyopadhyay, Chandrakanta ^{[1
]}

机构：

[1] RK Mission Vivekananda Centenary Coll, Dept Chem, Kolkata 700118, W Bengal, India

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 16期

关键词：

Rearrangement; Organocatalysis; Chromone-3-carbanilide; 2-Aminochromone-3-carbaldehyde; Chroman-2,4-dione; 1-Benzopyran; 2-(N-METHYLANILINO)-3-FORMYLCHROMONE;

D O I：

10.1016/j.tetlet.2011.02.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(Arylamino)-4-oxo-4H-1-benzopyran-3-carbaldehyde rearranges to 4-oxo-4H-1-benzopyran-3-carbanilide when treated with glycine in the presence of formalin, but under similar conditions 2-(alkylamino)-4-oxo-4H-1-benzopyran-3-carbaldehyde rearranges to 3-alkylaminomethylenechroman-2,4-dione. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1946 / 1948

页数：3

共 50 条

[31] Efficient synthesis of alkyl 2-[2-(arylcarbonylimino)-3-aryl-4-oxo-1, 3-thiazolan-5-ylidene]-acetates
Issa Yavari
Maryam Sabbaghan
Khalil Porshamsian
Mohammad Bagheri
Safa Ali-Asgari
Zinatossadat Hossaini
Molecular Diversity, 2007, 11 : 81 - 85
[32] Efficient synthesis of alkyl 2-[2-(arylcarbonylimino)-3-aryl-4-oxo-1, 3-thiazolan-5-ylidene]-acetates
Yavari, Issa
Sabbaghan, Maryam
Porshamsian, Khalil
Bagheri, Mohammad
Ali-Asgari, Safa
Hossaini, Zinatossadat
MOLECULAR DIVERSITY, 2007, 11 (02) : 81 - 85
[33] THERMAL REARRANGEMENT OF N-ALKYL-(2,2-DIHALO-1-PHENYLCYCLOPROPYL)METHYLENEAMINE, N-ARYL-(2,2-DIHALO-1-PHENYLCYCLOPROPYL)METHYLENEAMINE TO 1-ALKYL-2-HALO-4-PHENYLPYRROLE OR 1-ALKYL-3-HALO-4-PHENYLPYRROLE, AND 1-ARY L-2-HALO-4-PHENYLPYRROLE OR 1-ARYL-3-HALO-4-PHENYLPYRROLE
KAGABU, S
TSUJI, H
KAWAI, I
OZEKI, H
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (01) : 341 - 349
[34] Antibacterial 4-amino-N-(5-methylisoxazol-3-yl)-N-[(4-oxo-2-phenyl-4H-1-benzopyran-6-yl)methyl]benzenesulfonamide
Özbey, S
Akbas, A
Ayhan-Kilcigil, G
Ertan, R
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 : O559 - O561
[35] INVESTIGATION IN THE CHROMONE SERIES .23. REACTIVITY OF THE ESTERS OF 4-OXO-4H-1-BENZOPYRAN-2-CARBOXYLIC AND 4-OXO-4H-1-BENZOPYRAN-3-CARBOXYLIC ACID WITH DIPHENYLPHOSPHOROHYDRAZIDE AND DIPHENYLTHIOPHOSPHOROHYDRAZIDE
NAWROTMODRANKA, J
POLISH JOURNAL OF CHEMISTRY, 1995, 69 (09) : 1250 - 1256
[36] HETEROCYCLIC-SYSTEMS .10. DEFUNCTIONALIZATION OF "4-OXO-4H-[1]BENZOPYRAN-3-CARBOXYLIC ACIDS AND 4-OXO-4H-[1]BENZOPYRAN-3-CARBOXALDEHYDES
GHOSH, CK
KHAN, S
SYNTHESIS-STUTTGART, 1981, (09): : 719 - 721
[37] 4-OXO-1,2,3,4-TETRAHYDROQUINAZOLINES .2. SYNTHESIS OF 1-ALKYL- AND 1-[2-(DISUBSTITUTED AMINO)ETHYL]-2-METHYL-3-ARYL-4-OXO-1,2,3,4-TETRAHYDROQUINAZOLINES
OKUMURA, K
OINE, T
YAMADA, Y
HAYASHI, G
NAKAMA, M
NOSE, T
JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (04) : 788 - &
[38] HETEROCYCLIC SYSTEM .7. REACTIONS OF 4-OXO-4H-[1]BENZOPYRAN-3-CARBOXALDEHYDE AND "4-OXO-4H-[1]BENZOPYRAN-3-CARBOXYLIC ESTER WITH GUANIDINE
GHOSH, CK
KHAN, S
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1979, 18 (02): : 128 - 130
[39] CONVERSION OF ESTERS OF 2-OXO-2H-1-BENZOPYRAN-3-CARBOXYLIC ACIDS INTO ESTERS OF 2-OXO-4-CHROMANACETIC ACID - NEW REARRANGEMENT
IVANOV, C
BOJILOWA, A
CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (12): : 3755 - 3763
[40] SYNTHESIS AND CHARACTERIZATION OF BIVALENT-METAL COMPLEXES OF 4-OXO-4H-1-BENZOPYRAN-3-(CARBOXALDEHYDEPENTANOYLHYDRAZONE) (BPH) AND 4-OXO-4H-1-BENZOPYRAN-3-(CARBOXALDEHYDE-2-METHYL PROPIONYLHYDRAZONE) (BMPH)
NAWAR, N
KHATTAB, MA
BEKHEIT, MM
ELKADDAH, AH
SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1994, 24 (08): : 1281 - 1295

← 1 2 3 4 5 →