122687-60-9

Upstream product

• 98-91-9 thiobenzoic acid 
• 108805-12-5 3'-(Dimethylamino)spiroazirin> 
• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 50484-00-9 N,N-dimethyl cyclopentylcarboxamide 
• 3400-45-1 cyclopentanecarboxylic acid 

Downstream Products

• 158046-97-0 Ethyl-(10-(<(ethoxycarbonyl)methyl>thio)-7-phenyl-8-thia-6-azaspiro<4.5>deca-6.9-dien-9-carboxylat) 
• 138197-22-5 4,4,12-Triphenyl-1,3,13-trithia-11-azadispiro<4.0.4.3>tridec-11-en 
• 132900-68-6 2-Methyl-12-phenyl-1-oxa-4,13-dithia-11-azadispiro<4.0.4.3>tridec-11-en 
• 138197-17-8 1,1,3,3-Tetramethyl-12-phenyl-5,14,16-trithia-12-azatrispiro<3.1.0.4.3.2>hexadec-12-en-2-on 
• 80232-86-6 2-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazole 

Relevant academic research and scientific papers

218. Hetero-Diels-Alder Reaction with 1,3-thiazol-5(4H)-Thiones

On heating in toluene to 180 deg and on treatment with BF3*Et2O in CH2Cl2 at room temperature, 1,3-dienes react with the C=S group of 1,3-thiazol-5(4H)-thiones 1 in a reversible Diels-Alder reaction to give spiroheterocycles of type 6.A 1:1 mixture of two regioisomeric cycloadducts is formed in the thermal reaction with 2-methylbuta-1,3-diene (isoprene, 5b).In contrast, the formation of one regioisomer is strongly preferred in the BF3-catalyzed reaction.Frontier-orbital control as well as steric factors seem to be responsible for the observed regioselectivity.BF3-Catalyzed, cyclic 1,3-dienes and 1 also undergo a smooth Diels-Alder reaction.Whereas cyclohexa-1,3-diene (5c) reacts with 1a and 1b to give a single isomer (presumably the 'exo'-adduct), cyclopenta-1,3-diene (5d) leads to a ca. 3:1 mixture of 'exo'- and 'endo'-isomer.