摘要:

AbstractResynthesis of NSC 341,964, which had been assigned structure1(1‐[[3‐(7‐chloro‐4‐oxo‐4H‐3,1‐benzoxazin‐2‐yl)phenyl]methyl]pyridinium chloride) was approachedvia7‐chloro‐2‐(3‐methylphenyl)‐4H‐3,1‐benzoxazin‐4‐one (5) obtained from 3‐methylbenzoyl chloride (2) and 2‐amino‐4‐chlorobenzoic acid (3) followed by dehydration in acetic anhydride. Radical bromination provided6which with pyridine afforded the bromide analog7of1. Ion exchange, however, gave ring‐opened benzoic acid8rather than1. The original sample of NSC 341,964 also proved to be ring‐opened material. However,7upon standing exhibited slow hydrolysis to8so that the structure of the original NSC 341,964 remains uncertain.

ISSN:0022-152X    

DOI:10.1002/jhet.5570230151

出版商:Wiley‐Blackwell    

年代:1986

数据来源: WILEY

摘要:

Abstract2‐Methyl‐5‐(5‐oxo‐1‐benzyl‐2‐pyrrolidinyl)‐1,3,4‐oxadiazole is easily obtained by dehydration ofN‐acetyl‐1‐benzylpyroglutamic acid hydrazide with a methanesulfonic acid/pho

ISSN:0022-152X    

DOI:10.1002/jhet.5570230152

出版商:Wiley‐Blackwell    

年代:1986

数据来源: WILEY

摘要:

AbstractSulfur or nitrogen analogues of monooxo crown ethers were preparedviaintramolecular cyclization of the corresponding thia or aza oligoethylene glycol carboxylmethyl ethers by using benzenesulfonyl chloride in the presence of alkali metal carbonates.

ISSN:0022-152X    

DOI:10.1002/jhet.5570230153

出版商:Wiley‐Blackwell    

年代:1986

数据来源: WILEY

摘要:

AbstractCertain 3‐substituted derivatives of cyproheptadine (1a) have been shown to possess potent pharmacological properties. The structural analogy between cyproheptadine and azatadine (2) prompted the preparation of 9‐substituted derivatives of2and its 5,6‐dehydro analog for pharmacological comparison. The 9‐cyano and 9‐trifluoromethylthio derivatives were prepared by direct displacement of the corresponding 9‐bromo compounds. Acid hydrolysis of the nitriles generated the carboxylic acids. Oxidation of the trifluoromethylthio compounds15aand18agave the epoxy sulfones19aand19b, which could not be deoxygenated. Therefore, the trifluoromethylsulfonyl moiety was introduced prior to the formation of the exocy

ISSN:0022-152X    

DOI:10.1002/jhet.5570230154

出版商:Wiley‐Blackwell    

年代:1986

数据来源: WILEY

摘要:

AbstractFluradoline (2‐fluoro‐11‐[β‐(methylamino)ethylthio]dibenz[b,f]oxepin), a novel analgesic with an unique profile, was found to be extensively metabolized in man as well as in other species. One of the major metabolites of this drug appeared to be a nuclear hydroxylated derivative of the parent compound, and the site of enzymatic hydroxylation was established to be C(7) by using high‐field proton nuclear magnetic spectroscopy. This structural assignment was subsequently confirmed by the synthesis of an authentic sample of 2‐fluoro‐7‐hydroxy‐11‐[β‐(methylamino)ethylthio

ISSN:0022-152X    

DOI:10.1002/jhet.5570230155

出版商:Wiley‐Blackwell    

年代:1986

数据来源: WILEY

摘要:

AbstractAcyclovir was synthesized in five steps from 7‐formamido‐5‐methylthiofurazano[3,4‐d]pyrimidine2. Alkylation of2with 2‐(benzoyloxy)ethoxymethyl chloride, followed by reductive cleavage of the furazan ring gave 9‐[[2‐(benzoyloxy)ethoxy]methyl]‐2‐(methylthio)adenine5. Hydrolysis of the 6‐amino group of5, followed by amination of7with ammonia gave 9‐[(2‐hydroxyethoxy)methyl

ISSN:0022-152X    

DOI:10.1002/jhet.5570230156

出版商:Wiley‐Blackwell    

年代:1986

数据来源: WILEY

摘要:

AbstractWe have found previously that two 5‐acetyl‐4‐methylpyrimidines could be transformed by aminoguanidine hydrochloride into 4‐acetyl‐1‐amidino‐3‐methylpyrazolyl amidinohydrazone dihydrochloride. This reaction beside the fact that it led to a molecule closely related to the antitumor drug M.G.B.G. pointed out to a new possibility of ring contraction of pyrimidines into pyrazoles. We attempted therefore to study the possibility of extending this transformation to other substituted hydrazines and to define more accurately the conditions of this reaction as well as to prepare new potential a

ISSN:0022-152X    

DOI:10.1002/jhet.5570230157

出版商:Wiley‐Blackwell    

年代:1986

数据来源: WILEY

摘要:

AbstractThe reactions of 3‐methyl‐2‐oxo‐1,2‐dihydroquinoxaline3with chlorophenyl diazonium salts afforded the hydrazones4a‐c, whose chlorinations with phosphoryl chloride gave the dichlorides5a‐c. Refluxing of the dichlorides5a‐cand base inN,N‐dimethylformamide provided the 1‐aryl‐1H‐pyrazolo

ISSN:0022-152X    

DOI:10.1002/jhet.5570230158

出版商:Wiley‐Blackwell    

年代:1986

数据来源: WILEY

摘要:

AbstractEach reaction ofdl‐1,3‐dimethylthymine epoxide (1) with L‐amino acid ethyl esters (Pro‐OEt, Met‐OEt, Phe‐OEt, and Trp‐OEt) afforded the respective four optically active diastereomers4–7, stereo structures of which were definitely elucidated as shown in Chart 1 by an X‐ray analysis of4Aa

ISSN:0022-152X    

DOI:10.1002/jhet.5570230159

出版商:Wiley‐Blackwell    

年代:1986

数据来源: WILEY

摘要:

AbstractFrom (S)‐pyroglutamic acid (1) the asymmetric synthesis of (S)‐5‐ethyl‐2‐pyrrolidinone (5) in 30% yield is

ISSN:0022-152X    

DOI:10.1002/jhet.5570230160

出版商:Wiley‐Blackwell    

年代:1986

数据来源: WILEY