Efficient Synthesis of Highly Fused Quinazolinone Derivatives via Multiple C-C Bond Formations and 1,4-Palladium Migration

被引：2

作者：

Thavaselvan, Sampath ^{[1
]}

Arumugam, Natarajan ^{[2
]}

Almansour, Abdulrahman I. ^{[2
]}

Mahalingam, Sakkarapalayam M. ^{[3
]}

Parthasarathy, Kanniyappan ^{[1
]}

机构：

[1] Univ Madras, Dept Organ Chem, Guindy Campus, Chennai 025, Tamilnadu, India

[2] King Saud Univ, Coll Sci, Dept Chem, POB 2455, Riyadh 11451, Saudi Arabia

[3] Purdue Univ, Dept Chem, 720 Clin Dr, W Lafayette, IN 47907 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 06期

关键词：

C-H activation; annulation; palladium-catalyst; 1,4-palladium migration; alkyne; quinazolinone; CROSS-COUPLING REACTIONS; NICKEL-CATALYZED CYCLIZATION; H BOND; ROLLOVER CYCLOMETALATION; BICYCLIC ALKENES; ANNULATION; ALKYNES; PALLADIUM; ACTIVATION; COMPLEXES;

D O I：

10.1002/ejoc.202301023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient palladium-catalyzed annulation of 3-arylquinazolinones with mono and double alkyne insertion was developed for the synthesis of fused quinazolinone derivatives in 43-80 % yields. A notable effect was observed in product yield, when bases/additives were modulated. The reaction mechanism is believed to proceed through C-X cleavage/alkyne insertion/1,4-Pd migration and C-H annulation in a one-pot manner. We have developed a mild and efficient palladium-catalyzed annulation of 3-(2-halophenyl)quinazolin-4(3H)-ones with alkyne was developed for the synthesis of fused quinazolinone derivatives in 43-80 % yields. Notably, we observed remarkable changes in the product yield by modulating bases/additives.image

引用

页数：6

共 80 条

[1]

AlvarezBuilla J, 2011, MODERN HETEROCYCLIC CHEMISTRY, VOL 4, P1, DOI 10.1002/9783527637737

[2] Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C-H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates [J].

Bellina, Fabio ;

Rossi, Renzo .

TETRAHEDRON, 2009, 65 (50) :10269-10310

[3] Through-Space 1,4-Palladium Migration and 1,2-Aryl Shift: Direct Access to Dibenzo[a,c]carbazoles through a Triple C-H Functionalization Cascade [J].

Bhunia, Samir Kumar ;

Polley, Arghya ;

Natarajan, Ramalingam ;

Jana, Ranjan .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (47) :16786-16791

[4] "Rollover" cyclometalation - early history, recent developments, mechanistic insights and application aspects [J].

Butschke, Burkhard ;

Schwarz, Helmut .

CHEMICAL SCIENCE, 2012, 3 (02) :308-326

[5] Novel 1,4-palladium migration in organopalladium intermediates derived from o-iodobiaryis [J].

Campo, MA ;

Larock, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) :14326-14327

[6] Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds [J].

Cherney, Alan H. ;

Kadunce, Nathaniel T. ;

Reisman, Sarah E. .

CHEMICAL REVIEWS, 2015, 115 (17) :9587-9652

[7] Multi-component syntheses of heterocycles by transition-metal catalysis [J].

D'Souza, Daniel M. ;

Mueller, Thomas J. J. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1095-1108

[8] Palladium Catalyzed Cross-Dehydrogenative Coupling/Annulation Reaction: A Practical and Efficient Approach to Hydroxyisoindolo[1,2-b]quinazolinone [J].

Dabiri, Minoo ;

Lehi, Noushin Farajinia ;

Movahed, Siyavash Kazemi ;

Khavasi, Hamid Reza .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (18) :2933-2940

[9] Pd-Catalyzed regioselective C-H halogenation of quinazolinones and benzoxazinones [J].

Dabiri, Minoo ;

Lehi, Noushin Farajinia ;

Movahed, Siyavash Kazemi ;

Khavasi, Hamid Reza .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (29) :6264-6268

[10] Recent Advances in Ruthenium(II)-Catalyzed C-H Bond Activation and Alkyne Annulation Reactions [J].

Duarah, G. ;

Kaishap, P. P. ;

Begum, T. ;

Gogoi, S. .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (04) :654-672

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