66607-51-0

Upstream product

• 62-53-3 aniline 
• 51550-17-5 5,6,7,8-tetrahydro-2-(methylthio)<1>benzothieno<2,3-d>pyrimidin-4(1H)-one 
• 64-19-7 acetic acid 
• 168280-54-4 3-amino-2-phenylamino-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 4506-71-2 ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 622-34-4 1-phenylcyanamide 

Downstream Products

• 143770-17-6 5-phenylamino-8,9,10,11-tetrahydro<1>benzothieno<3,2-e>tetrazolo<1,5-c>pyrimidine 
• 143770-31-4 4-amino-2-phenylamino-5,6,7,8-tetrahydro<1>benzothieno<2,3-d>pyrimidine 
• 143770-12-1 4-chloro-2-phenylamino-5,6,7,8-tetrahydro<1>benzothieno<2,3-d>pyrimidine 

Relevant academic research and scientific papers

Title studies on the reaction of N-(3-carbethoxy-4,5,6,7-tetrahydrobenzo[b] thien-2-yl)-N′-phenylthiourea with hydrazine hydrate (Part 1)

(Chemical Equation Presented) The reaction of N-(3-carbethoxy-4,5,6,7- tetrahydrobenzo[b]thien-2-yl)-N′-phenylthiourea (1) with hydrazine hydrate in 1-butanol afforded a mixture of compounds 2, 3 and 4. Treatment of 3 and 4 with nitrous acid gave 6 and 8 respectively, while reactions of 3 with acetylacetone gave 7. Synthesis of tetracyclic compounds 9a-f and 11 from the reactions of 3 with ethyl orthoformate or appropriate acids, acid chloride, carbon disulphide and/or ethyl chloroformate. Also its reaction with isothiocyanate derivatives gave the corresponding thiosemicarbzides 12a,b which on, refluxing in alcoholic KOH gave the unexpected tetracyclic products 14a,b. Similarly the tetracyclic compounds 16a-e and 19 were obtained by cyclization of 4 and 18 respectively.

Reaction of Nitriles Under Acidic Conditions. Part III. A Facile Synthesis of Thienopyrimidin-4(3H)-ones

A variety of thiophene o-aminoesters were reacted with cyanates, thiocyanates, cyanamides, acyl cyanides and α-functionalized acetonitrile derivatives to yield the corresponding 2-substituted thienopyrimidin-4(3H)-ones.

Synthesis of 2-Amino- and 2-Guanidinothienopyrimidin-4(3H)-ones

Cyanamide and 1-arylcyanamides (2a-f) react with ethyl 2-aminothiophene-3-carboxylate (1a, R,R'= -(CH2)4-) to give 2-amino- and 2-arylaminothienopyrimidin-4(3H)-ones (3a-f, R''= H or Ar).A similar reaction of dicyandiamide (4a) and aryldicyandiamides (4b-f) with 1a gives 2-guanidino-thienopyrimidin-4(3H)-ones (5a-f, R''= H or Ar).However, ethyl 2-amino-4-methyl-5-(N-phenylcarboxamido)thiophene-3-carboxylate (1b, R = Me, R'= CONHPh) and ethyl 4-amino-2-imino-3-phenylthiazoline-5-carboxylate fail to give similar thieno- and thiazolo-pyrimidinones.Several new 2-(N-arylguanidino)quinazolin-4(3H)-ones (6a-e, R''= aryl) have been obtained from methyl anthranilate and aryldicyandiamides (4b-f).