Direct access to novel chromeno-pyrimidine-N-oxides via tandem base catalyzed double nucleophilic addition/dehydration reaction

被引：9

作者：

Jalli, Venkata Prasad ^{[1
]}

Jaggavarapu, Satyanarayana Reddy ^{[1
]}

Kamalakaran, Anand Solomon ^{[1
]}

Gangisetty, Sravan Kumar ^{[1
]}

Nanubolu, Jagadeesh Babu ^{[2
]}

Gaddamanugu, Gopikrishna ^{[1
]}

机构：

[1] Sankar Fdn Res Inst, Dept Chem, Visakhapatnam 530047, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Xray Crystallog Div, Hyderabad 500076, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 11期

关键词：

Pyrimidine-N-oxides; 4-Chloro-3-formylcoumarin; Carboximide oxime; Chromeno-pyrimidine-N-oxide; Tandem; MINOXIDIL SULFATE; DERIVATIVES; REARRANGEMENTS; MECHANISMS;

D O I：

10.1016/j.tetlet.2013.01.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile protocol for direct access to chromeno-pyrimidine-N-oxides is reported by the reaction of 4-chloro-3-formylcoumarin and aromatic carboximide oximes via tandem double nucleophilic addition and dehydration reactions. The one-pot reaction serves as an alternative protocol for achieving regioselective pyrimidine mono-N-oxide products as pure precipitates in good to excellent yields. The structure of the product was confirmed by X-ray analysis. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：1491 / 1494

页数：4

共 40 条

[21] KIM KM, 1993, SYNTHESIS-STUTTGART, P283
[22] THE SYNTHESIS OF PYRIMIDINE 1-OXIDES - A NEW TRANSFORMATION OF AMIDE OXIMES
KOCEVAR, M
MLAKAR, B
PERDIH, M
PETRIC, A
POLANC, S
VERCEK, B
[J]. TETRAHEDRON LETTERS, 1992, 33 (16) : 2195 - 2198
[23] ENZYMATIC AND NONENZYMATIC SULFATION MECHANISMS IN THE BIOLOGICAL ACTIONS OF MINOXIDIL
MEISHERI, KD
JOHNSON, GA
PUDDINGTON, L
[J]. BIOCHEMICAL PHARMACOLOGY, 1993, 45 (02) : 271 - 279
[24] MEISHERI KD, 1988, J PHARMACOL EXP THER, V245, P751
[25] Minoxidil: mechanisms of action on hair growth
Messenger, AG
Rundegren, J
[J]. BRITISH JOURNAL OF DERMATOLOGY, 2004, 150 (02) : 186 - 194
[26] Carboxamide oximes as convenient precursors for the synthesis of pyrimidine N-oxides
Mlakar, B
Stefane, B
Kocevar, M
Polanc, S
[J]. TETRAHEDRON, 1998, 54 (17) : 4387 - 4396
[27] Cascade reactions in total synthesis
Nicolaou, K. C.
Edmonds, David J.
Bulger, Paul G.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) : 7134 - 7186
[28] Tandem reactions, cascade sequences, and biomimetic strategies in total synthesis
Nicolaou, KC
Montagnon, T
Snyder, SA
[J]. CHEMICAL COMMUNICATIONS, 2003, (05) : 551 - 564
[29] Tandem methodology for heterocyclic synthesis
Padwa, A
[J]. PURE AND APPLIED CHEMISTRY, 2004, 76 (11) : 1933 - 1952
[30] Efficient catalyst-free Domino approach for the synthesis of novel 2-benzazepine derivatives in water
Prasad, J. Venkata
Prabhakar, Maddela
Manjulatha, K.
Rambabu, D.
Solomon, K. Anand
Krishna, G. Gopi
Kumar, K. Anil
[J]. TETRAHEDRON LETTERS, 2010, 51 (23) : 3109 - 3111

← 1 2 3 4 →