Journal ArticleDOI
Synthesis and reactions of 2-hetero-4H-3,1-benzoxazin-4-ones
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In this paper, the synthesis and reactions of 2-hetero-4H-3,1-benzoxazin-4-ones which include oxygen, sulfur and nitrogen substituents are reviewed.About:
This article is published in Journal of Heterocyclic Chemistry.The article was published on 2000-11-01. It has received 30 citations till now. The article focuses on the topics: Sulfur.read more
Citations
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Journal ArticleDOI
Room‐Temperature Palladium‐Catalyzed C ? H Activation: ortho‐Carbonylation of Aniline Derivatives
Chris E. Houlden,Marc Hutchby,Christopher Bailey,J. Gair Ford,Simon N. G. Tyler,Michel R. Gagné,Guy C. Lloyd-Jones,Kevin I. Booker-Milburn +7 more
TL;DR: The title reaction proceeds efficiently at 18 degrees C under CO (1 atm) with 5 % [Pd(OTs)(2)(MeCN)(2)] as precatalyst with high yields.
Journal ArticleDOI
Palladium-catalyzed carbonylative synthesis of benzoxazinones from N-(o-bromoaryl)amides using paraformaldehyde as the carbonyl source.
Wanfang Li,Xiao-Feng Wu +1 more
TL;DR: A series of substituted benzoxazinones were synthesized from N-(o-bromoaryl)amides by palladium-catalyzed carbonylation with paraformaldehyde as the carbonyl source, which is inexpensive, stable, and easy to use.
Book ChapterDOI
Pyrimidines and their Benzo Derivatives
TL;DR: The chemistry of pyrimidines and their benzo derivatives, including quinazolines, perimidines, and benzo[gh]perimidine is reviewed in this article, with particular attention paid to work published between 1996 and 2007.
Journal ArticleDOI
A convenient and general palladium-catalyzed carbonylative coupling for the synthesis of 2-arylbenzoxazinones.
TL;DR: A new double carbonylation procedure is presented, which allows for a general synthesis of 2(hetero)arylbenzoxazinones starting from easy available 2bromoanilines and (heterO)aryl bromides.
Journal ArticleDOI
A Convenient Palladium-Catalyzed Carbonylative Synthesis of 2-Aminbenzoxazinones from 2-Bromoanilines and Isocyanates
Xiao-Feng Wu,Xiao-Feng Wu,Muhammad Sharif,Muhammad Sharif,Khurram Shoaib,Helfried Neumann,Anahit Pews-Davtyan,Peter Langer,Matthias Beller +8 more
TL;DR: A general and convenient methodology for 2-aminobenzoxazinone synthesis has been developed and various products have been prepared in good yields using [Mo(CO)6] as a solid CO source.
References
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Journal ArticleDOI
Design and synthesis of 4H-3,1-benzoxazin-4-ones as potent alternate substrate inhibitors of human leukocyte elastase.
Allen Krantz,Robin W. Spencer,Tim Fat Tam,Liak Teng J,Leslie J. Copp,Everton Thomas,Steven P. Rafferty +6 more
TL;DR: It is concluded that chemically stable, potent benzoxazinone inhibitors of HL elastase with inhibition constants in the nanomolar range can be designed with (1) R5 alkyl groups to inhibit enzyme-catalyzed deacylation, and (2) strongly electron-donating groups at C7 to stabilize the oxazin one ring to nucleophilic attack.
Journal ArticleDOI
2-amino-4H-3,1-benzoxazin-4-ones as inhibitors of C1r serine protease.
Sheryl J. Hays,Bradley William Caprathe,John L. Gilmore,Nilam Amin,Mark R. Emmerling,Walter Michael,Ravi Nadimpalli,Rathna Nath,Kadee J. Raser,Daniel Stafford,Desiree Watson,Kevin K.W. Wang,Juan C. Jaen +12 more
TL;DR: A series of 2-amino-4H-3,1-benzoxazin-4-ones have been synthesized and evaluated as inhibitors of the complement enzyme C1r, and many of these active compounds show improved potency compared to the reference compound FUT-175.
Journal ArticleDOI
Suicide inactivation of chymotrypsin by benzoxazinones.
TL;DR: The mechanism of inactivation involves attack of the active site serine on the C-4 carbonyl of the inactivator which leads to ring opening and formation of an ortho-substituted benzoylchymotrypsin, which hydrolyzes slowly due to electron releasing ability of the substituents.
Journal ArticleDOI
Inhibition of HSV-1 protease by benzoxazinones
Richard L. Jarvest,Martin J. Parratt,Christine Debouck,Joselina G. Gorniak,L.John Jennings,Halina T. Serafinowska,James E. Strickler +6 more
TL;DR: Benzoxazinones have been discovered which are mechanism based inhibitors of HSV-1 protease with micromolar IC 50 values and a parallel array synthesis was developed to explore 2-heteroatom substituted SAR.
Journal ArticleDOI
A new class of heterocyclic serine protease inhibitors. Inhibition of human leukocyte elastase, porcine pancreatic elastase, cathepsin G, and bovine chymotrypsin A alpha with substituted benzoxazinones, quinazolines, and anthranilates.
T Teshima,J C Griffin,J C Powers +2 more
TL;DR: The results indicate that it is possible to develop non-peptide small molecules which are specific inhibitors for HL elastase and the partially polarized carbonyl group of the inhibitor interacts with a partially polarized charge relay system of the serine protease.