62882-01-3

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 2631, 1993 DOI: 10.1021/jo00061a046

InChI:InChI=1/C10H9N/c1-8-3-2-4-9-7-11-6-5-10(8)9/h2-7H,1H3

Upstream product

• 100643-54-7 5-methyl-3,4-dihydro-isoquinoline 
• 7372-92-1 7-methyl-1H-indene 
• 34784-04-8 5-bromoisoquinoline 
• 55755-16-3 2-methylphenethylamine 
• 857822-30-1 2-(2-methylphenyl)ethylformamide 
• 137203-34-0 bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct 

Downstream Products

• 80278-67-7 isoquinoline-5-carboxaldehyde 
• 1367744-24-8 5-methylisoquinoline-1-carbonitrile 

Relevant academic research and scientific papers

User-friendly methylation of aryl and vinyl halides and pseudohalides with DABAL-Me3

An extremely technically simple cross-methylation of aryl and vinyl halides and pseudohalides using an air-stable adduct of trimethylaluminium with a Pd(0) catalyst supported by commercially available biarylphosphines gives excellent yields of methylated products (mainly > 95%). Reactions can be run with either 0.5 mol% catalyst or without requiring the exclusion of atmospheric oxygen or the drying of solvents in some cases. A wide variety of functional groups is tolerated including CN, OH, CO2R, CHO and NO2.

ANTITHROMBOTIC AMIDINOTETRAHYDROPYRIDYLALANINE DERIVATIVES

This invention is directed to compounds of formula (I), STR1 pharmaceutically acceptable salts thereof, and pharmaceutically acceptable solvates of either entity, wherein Y is optionally monounsaturated C 3-C 5 alkylene optionally substituted with C. sub.1-C 4 alkyl or methylene; R 1 is H; C 1-C 4 alkyl optionally substituted with C 1-C 4 alkoxy, OH, NR 5 R 6, CONR 5 R 6, C 3-C 6 cycloalkyl or aryl; or C 3-C 6 alkenyl; R 2 is H; C 1-C 4 alkyl optionally substituted with C 1-C 4 alkoxy, OH, NR 5 R 6, CONR 5 R 6, C 3-C 6 cycloalkyl or aryl; or CONR 5 R 6 ; R. sup.3 and R 4 are each independently selected from H; C 1-C. sub. 4 alkyl optionally substituted with NR 5 R 6 ; C 1-C. sub.4 alkoxy; halo; CONR 5 R 6 and aryl; aryl is phenyl optionally substituted with one, two or three substituents independently selected from C 1-C 4 alkyl, C 1-C 4 alkoxy, OH, halo and CF 3 ; R 5 and R 6 are each independently selected from H and C 1-C 4 alkyl; and m and n are each independently 1, 2 or 3; which are potent and selective thrombin inhibitors useful in the treatment of inter alia, deep vein thrombosis; reocclusion following thrombolytic therapy; chronic arterial obstruction; peripheral vascular disease; acute myocardial infarction; unstable angina; atrial fibrillation; thrombotic stroke; transient ischaemic attacks; restenosis and occlusion following angioplasty; or neurodegenerative disorders.

Synthesis of Isoquinolines from Indenes

A general procedure for the synthesis of isoquinolines from appropriately substituted indenes is described.Ozonolysis of the indenes followed by reductive workup gives intermediate homophthalaldehydes which are treated with ammonium hydroxide to give the isoquinolines.This "one-pot", three-step reaction sequence was applied to the formation of all of the mono-C-methyl-substituted isoquinolines in a regiospecific manner.The procedure is applicable to both electron-withdrawing and electron-donating substituents on the indene system.In this manner the 6- and 7-nitro-,-bromo-, and -iodoisoquinolines were prepared.