Pd/C-mediated synthesis of α-pyrone fused with a five-membered nitrogen heteroaryl ring: A new route to pyrano[4,3-c]pyrazol-4(1H)-ones

被引：15

作者：

Gorja, Dhilli Rao ^{[2
]}

Batchu, Venkateswara Rao ^{[3
]}

Ettam, Ashok ^{[3
]}

Pal, Manojit ^{[1
]}

机构：

[1] Matrix Labs Ltd, R&D Ctr, New Drug Discovery, Jinnaram Mandal 502325, Andhra Pradesh, India

[2] JNT Univ, Inst Sci & Technol, Hyderabad 500072, Andhra Pradesh, India

[3] Dr Reddys Labs Ltd, Hyderabad 500049, Andhra Pradesh, India

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 5卷

关键词：

C-C bond; catalysis; palladium; pyrazole; pyrone; PALLADIUM-CATALYZED HETEROANNULATION; O-IODOBENZOIC ACID; TERMINAL ALKYNES; ISOCOUMARINS; CYCLIZATION; PHTHALIDES;

D O I：

10.3762/bjoc.5.64

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd/C-mediated alkynylation of 5-iodo-pyrazole-4-carboxylic acid, involving the first regioselective construction of alpha-pyrone ring on a pyrazol moiety via tandem coupling-cyclization process, has been developed to afford pyrano[4,3-c]pyrazol-4(1H)-one in a single pot.

引用

页数：5

共 21 条

[1] ISOCOUMARINS - DEVELOPMENTS SINCE 1950 [J].

BARRY, RD .

CHEMICAL REVIEWS, 1964, 64 (03) :229-+

[2] New procedures for the selective synthesis of 2(2H)-pyranone derivatives and 3-aryl-4-iodoisocoumarins [J].

Biagetti, M ;

Bellina, F ;

Carpita, A ;

Stabile, P ;

Rossi, R .

TETRAHEDRON, 2002, 58 (25) :5023-5038

[3] Rapid access to pyrazolo[3,4-c]pyridines via alkyne annulation:: Limitations of steric control in nickel-catalyzed alkyne insertions [J].

Heller, Stephen T. ;

Natarajan, Swaminathan R. .

ORGANIC LETTERS, 2007, 9 (24) :4947-4950

[4]

Hussain MT, 2001, INDIAN J CHEM B, V40, P372

[5] SYNTHESIS OF PHTHALIDES THROUGH PALLADIUM-CATALYZED HETEROANNULATION OF ACETYLENIC-COMPOUNDS [J].

KUNDU, NG ;

PAL, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (01) :86-88

[6] Palladium-catalysed heteroannulation with terminal alkynes: synthesis of phthalides [J].

Kundu, NG ;

Pal, M ;

Nandi, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03) :561-568

[7] SYNTHESIS OF ISOCOUMARINS FROM O-IODOBENZOIC ACID AND TERMINAL ACETYLENES MEDIATED BY PALLADIUM COMPLEXES AND ZINC-CHLORIDE [J].

LIAO, HY ;

CHENG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3711-3716

[8] 2-Pyrone natural products and mimetics: isolation, characterisation and biological activity [J].

McGlacken, GP ;

Fairlamb, IJS .

NATURAL PRODUCT REPORTS, 2005, 22 (03) :369-385

[9]

NOZAWA K, 1981, CHEM PHARM BULL, V29, P2491

[10] Palladium-Catalyzed Alkynylation of Aryl and Hetaryl Halides: A Journey from Conventional Palladium Complexes or Salts to Palladium/Carbon [J].

Pal, Manojit .

SYNLETT, 2009, (18) :2896-2912

← 1 2 3 →