149125-65-5Relevant academic research and scientific papers
Benzannulation of triynes to generate functionalized arenes by spontaneous incorporation of nucleophiles
Karmakar, Rajdip,Yun, Sang Young,Chen, Jiajia,Xia, Yuanzhi,Lee, Daesung
supporting information, p. 6582 - 6586 (2015/06/02)
The thermal reaction of ester-tethered 1,3,8-triynes provides novel benzannulation products with concomitant incorporation of a nucleophile. Evidence suggests that this reaction proceeds via an allene-enyne intermediate generated by an Alder-ene reaction in the first step. Depending on the substituent of the alkyne moiety on the allene-enyne intermediate, the subsequent transformation can take one of two different paths, each leading to discrete aromatization products. The benzannulation of a silane-substituted 1,3,8-triynes provides arene products with a nucleophile incorporated onto the newly formed benzene core, whereas an aryl substituent leads to nucleophile trapping at the benzylic carbon atom connected to the aryl substituent. The formation of these two different products results from the involvement of two regioisomeric allene-enyne intermediates.
N-Substitution dependent stereoselectivity switch in palladium catalyzed hydroalkynylation of ynamides: A regio and stereoselective synthesis of ynenamides
Dwivedi, Vikas,Hari Babu, Madala,Kant, Ruchir,Sridhar Reddy, Maddi
supporting information, p. 14996 - 14999 (2015/10/12)
A highly general palladium catalysed regioselective hydroalkynylation of ynamides for versatile enamide building blocks with an alkyne tether is achieved with an N-substitution dependent stereoselectivity switch under very mild reaction conditions.
An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol
Clarke, Paul A.,Rolla, Gabriele A.,Cridland, Andrew P.,Gill, Andrew A.
, p. 9124 - 9128 (2008/02/10)
An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol has been devised. This new route increases the throughput and yield of the diene product by circumventing a low yielding preparation of boronic acid intermediate as well as removing the need to use multi-gram quantities of highly toxic thallium salts. In the process of developing this new route, a higher yielding preparation of (E)-3-hydroxyprop-1-enylboronic acid was also achieved.
4-Homopyrazofurin and an acyclic analogue
Sauer,Schneller,Gabrielsen
, p. 71 - 79 (2007/10/02)
The synthesis of 4-hydroxymethyl-3(5)-(β-D-ribofuranosyl)pyrazole-5(3)-carboxamide (2, 4-homopyrazofurin) is described via a pathway that commences with the dipolar cycloaddition reaction of 2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-diazo-D-allitol (4) and methyl 4-benzyloxy-2-butynoate (5). Preparation of 3(5)-[(2-hydrox,-ethoxy)methyl]-4-(hydroxymethyl)pyrazole-5(3)-carboxa mide (3) as a derivative of 2 possessing the truncated acyclic side chain of acyclovir has been accomplished in a similar manner beginning with the reaction of 5 with 1-diazo-2-[(2-benzyloxy)ethoxy]ethane (13). Neither compound 2 nor 3 showed any in vitro antiviral activity against human immunodeficiency virus (HIV-1), sandfly fever, Punta Toro, Japanese encephalitis, yellow fever, Venezuelan equine encephalomyelitis, and vaccinia viruses. Both compounds were also nontoxic. These results suggest that direct bonding of the hydroxyl group to the pyrazole ring is important for pyrazofurin based agents to demonstrate biological activity. The synthesis of 4-hydroxymethyl-3(5)- (β-D-ribofuranosyl)pyrazole-5(3)-carboxamide (2, 4-homo-pyrazofurin) is described via a pathway that commences with the dipolar cycloaddition reaction of 2,5-anhydro- 3,4,6-tri-O-benzyl-1-deoxy-1-diazo-D-allitol (4) and methyl 4-benzyloxy-2-butynoate (5). Preparation of 3(5)-[(2-hydrox,-ethoxy)methyl ]-4-(hydroxymethyl)pyrazole-5(3)-carboxamide (3) as a derivative of 2 possessing the truncated acyclic side chain of acyclovir has been accomplished in a similar manner beginning with the reaction of 5 with 1-diazo-2-[(2-benzyloxy)ethoxy]ethane (13). Neither compound 2 nor 3 showed any in vitro antiviral activity against human immunodeficiency virus (HIV-1), sandfly fever, Punta Toro, Japanese encephalitis, yellow fever, Venezuelan equine encephalomyelitis, and vaccinia viruses. Both compounds were also nontoxic. These results suggest that direct bonding of the hydroxyl group to the pyrazole ring is important for pyrazofurin based agents to demonstrate biological activity.
