e-book Compr. Heterocyclic Chem. III Vol. 8 Six-membered Rings with Two Heteroatoms

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Note that when the attachment point on the U group is illustrated as floating, the U group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the U group by replacement of a hydrogen atom. Note that some U groups can only be substituted with less than 4 R v groups e. A wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A.

Katritzky and C. Katritzky, C. Rees and E.

Aromatic heterocycles I - Aromatic Compounds - Organic chemistry - Khan Academy

Scriven editors-in-chief, Pergamon Press, Oxford, Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. Stereoisomers are isomers of identical constitution but differing in the arrangement of their atoms in space and include enantiomers, diastereomers, cis-trans isomers also known as geometric isomers and atropisomers.

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Atropisomers result from restricted rotation about single bonds where the rotational barrier is high enough to permit isolation of the isomeric species. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form. Compounds of this invention can exist as one or more conformational isomers due to stereochemistry of the double bond in Formula I. This invention comprises mixtures of conformational isomers. In addition, this invention includes compounds that are enriched in one conformer relative to others.

One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid MCPBA , hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.

These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. Gilchrist in Comprehensive Organic Synthesis, vol. Ley, Ed.

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol.


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Boulton and A. McKillop, Eds. Grimmett and B. Keene in Advances in Heterocyclic Chemistry, vol. Katritzky, Ed. Stanovnik in Advances in Heterocyclic Chemistry, vol. Katritzky and A.

Five-Membered Heterocycles with Two Heteroatoms

Boulton, Eds. Cheeseman and E. Werstiuk in Advances in Heterocyclic Chemistry, vol. One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms. The salts of a compound of Formula I include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.

When a compound of Formula I contains an acidic moiety such as a carboxylic acid or phenol, salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium.

Accordingly, the present invention comprises compounds selected from Formula I, N-oxides and salts thereof. Embodiments of the present invention as described in the Summary of the Invention include where Formula I as used in the following Embodiments includes N-oxides and salts thereof :. Embodiments of the present invention as described in the Summary of the Invention include the following:. Embodiment Al. A compound of Formula I as described in the Summary of Invention. Embodiment A2.

A compound of Embodiment Al wherein A is phenyl, naphthalenyl, or a 5- or 6-membered heterocyclic ring, each ring or ring system optionally substituted with halogen, -C4 alkyl, C3-C7 cycloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, -C4 alkoxy, -C4 haloalkyl, -C4 haloalkoxy or -C4 haloalkylthio. Embodiment A3. A compound of Embodiment A2 wherein A is phenyl, naphthalenyl, or a 5- or 6-membered heterocyclic ring, each ring or ring system optionally substituted with halogen or -C4 alkyl. Embodiment A4.

A compound of Embodiment A3 wherein A is phenyl, naphthalenyl, or a 5- or 6-membered heterocyclic ring, each ring or ring system optionally substituted with halogen. Embodiment A5. Embodiment A6. Embodiment A7. A compound of Embodiment A6 wherein A is phenyl, optionally substituted with halogen or -C4 alkyl. Embodiment A8. A compound of Embodiment A7 wherein A is phenyl, optionally substituted with halogen. Embodiment A9.

1. Introduction

A compound of Embodiment A8 wherein A is phenyl substituted with halogen at 3- and 5-positions or 2- and 5-positions. Embodiment A A compound of Embodiment A8 wherein A is phenyl, optionally substituted with up to 5 F. Embodiment Al 1. Embodiment A A compound of Embodiment A12 wherein A is a 5- or 6-membered heterocyclic ring, each ring optionally substituted with halogen or -C4 alkyl.

A compound of Embodiment A13 wherein A is a 5- or 6-membered heterocyclic ring, each ring optionally substituted with halogen. A compound of Embodiment Al wherein A is phenyl, 2-thienyl,. Embodiment Al 6. A compound of Embodiment Al 5 wherein A is phenyl or 2-thienyl, each optionally substituted with halogen or Q-C4 alkyl. A compound of Embodiment A16 wherein A is phenyl or 2-thienyl, each optionally substituted with halogen.

C4 alkoxy; or phenyl, naphthalenyl or a 5- or 6-membered heterocyclic ring, each ring or ring system optionally substituted with halogen, Q-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Q-C4 alkoxy, -C4 haloalkyl or -C4 haloalkoxy.

Highlights on π-systems based on six-membered phosphorus heterocycles

Embodiment A20a. A compound of Embodiments A20 wherein R is phenyl, optionally substituted with -C4 alkyl. A compound of Embodiments A22 wherein R is 4-methylbenzene. Embodiment Bl. A method for preparing a compound of Formula I as described in the. Embodiment B2. A method of Embodiment Bl wherein A is phenyl, naphthalenyl, or a.

Embodiment B3. A method of Embodiment B2 wherein A is phenyl, naphthalenyl, or a 5- or 6-membered heterocyclic ring, each ring or ring system optionally substituted with halogen or Q-C4 alkyl. Embodiment B4. A method of Embodiment B3 wherein A is phenyl, naphthalenyl, or a 5- or 6-membered heterocyclic ring, each ring or ring system optionally substituted with halogen. C2-C4 di-alkylamino, cyano, nitro, -C4 alkoxy-carbonyl, phenyl or phenoxy. Embodiment B6.


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A method of Embodiment B5 wherein A is phenyl optionally. Embodiment BIO.